No renderable structure data available
C1=CC=C2C(=C1)C=C(N2)OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 1H-indol-2-ol |
|---|---|
| IUPAC Name | — |
| CAS Number | 16990-73-1 |
| Database ID | 65531 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
1H-indol-2-ol (CAS 16990-73-1) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 65531
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-4e950a96341b48d8bbf1147a919a245aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The hydroxyindole compound was readily prepared by a literature method (P. L. Southwick, J. G. Cairns, L. A. Ernst, and A. S. Waggoner, One pot Fischer synthesis of (2,3,3-trimethyl–3-H-indol–5-yl)-acetic acid derivatives as intermediates for fluorescent biolabels, Org. Prep. Proced. Int. Briefs, 1988, 20(3), 279–284). Reaction of p-carboxymethylphenylhydrazine hydrochloride (30 mmol, 1 equiv.) and 1,1-bis(hydroxymethyl)propanone (45 mmol, 1.5 equiv.) in acetic acid (50 mL) at room temperature for 30 minutes and at reflux for 1 gave (3,3-dihydroxymethyl2-methyl-3-H-indol-5-yl)-acetic acid as a solid residue. at reflux for 1
Source ID: ord-caf1b705e850426688527a5cd9cbc18bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The intermediate, 5-hydroxy-2-methyl-7-azaindole, was prepared as follows. A. To a solution of 5-methoxy-7-azaindole (240 mg, 1.62 mmol) in THF (10 mL) was added a 60% suspension of sodium hydride in oil (71 mg, 1.78 mmol) at RT under argon. The mixture was stirred at RT for 5 minutes and phenylsulphonyl chloride (250 μL, 1.95 mmol) was added and the mixture was stirred for 16 h, quenched with saturated ammonium chloride (20 mL) and extracted with ethyl acetate (3×25 μL). The combined organic layers were washed with brine (50 mL), dried, filtered and concentrated. The residue was purified by flash chromatography (1% MeOH in dichloromethane+0.5% triethylamine) to afford N-phenylsulphonyl-5-methoxy-7-azaindole (325 mg, 70%) as a solid. 1H NMR (400 MHz, CDCl3) δ 8.12 (3H, m), 7.65 (1H, dd, J=3.8), 7.54 (1H, m), 7.45 (2H, m), 7.28 (1H, d, J=2.8 Hz), 6.51 (1H, d, J=3.8 Hz), 3.82 (3H, s). (M+H)+=289. B. A solution (2.7M) of n-butyllithium in hexanes (0.48 mL, 1.30 mmol) was added to a solution of N-phenylsulphonyl-5-methoxy-7-azaindole (220 mg, 0.76 mmol) in THF (7.0 mL) at −78° C. under argon. The resulting solution was stirred at −78° C. for 1 h and methyl iodide (120 μL, 1.91 mmol) was added. The resulting mixture was stirred at −78° C. for 2 h, quenched with saturated ammonium chloride (20 mL) and extracted with ethyl acetate (3×25 mL). The combined organic layers were washed with brine (50 mL), dried, filtered and concentrated. The residue was purified by flash chromatography (1% MeOH in dichloromethane+0.1% triethylamine) to afford (170 mg, 73%) of a (5:1) mixture of N-phenylsulphonyl-5-methoxy-2-methyl-7-azaindole, m/z 303 (M+H+), analytical HPLC retention time=1.83 min and N-tolylsulphonyl-5-methoxy-2-methyl-7-azaindole, m/z 317, retention time=1.97 min. C. To a solution of above mixture of compounds in (3:1) THF-methanol (4 mL) was added a 10% solution of sodium hydroxide in water (3 mL) at room temperature. The mixture was heated to 65° C. for 1 h, cooled to room temperature, neutralized to pH 7 with a saturated ammonium chloride solution and extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with brine (50 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography on silica gel (1% MeOH in dichloromethane+0.1% triethylamine) to afford 5-methoxy-2-methyl-7-azaindole (35 mg, 66%). (M+H)+=163. D. The procedure described above for the preparation of hydroxyindole from methoxyindole in Example 1 was applied to 5-methoxy-2-methyl-7-azaindole (35 mg, 0.2 mmol) to afford 5-hydroxy-2-methyl-7-azaindole (32 mg, 100%) which was used directly without any further purification. LC/MS; (M+H)+=135.
Source ID: ord-b74fca6ef66c4c58ba5b56f7734efa7dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The hydroxy-indole compound is readily prepared by literature method (P. L. Southwick, J. G. Cairns, L. A. Ernst, and A. S. Waggoner, One pot Fischer synthesis of (2,3,3-trimethyl-3-H-indol-5-yl)-acetic acid derivatives as intermediates for fluorescent biolabels. Org. Prep. Proced. Int. Briefs, 1988, 20(3), 279-284). Reaction of p-carboxymethylphenylhydrazine hydrochloride (30 mmol, 1 equiv.) and 1,1-bis(hydroxymethyl)propanone (45 mmole, 1.5 equiv.) in acetic acid (50 mL) at room temperature for 30 minutes and at reflux for 1 gives (3,3-dihydroxymethyl2-methyl-3-H-indol-5-yl)-acetic acid as a solid residue. The reaction of 3-bromopropyl-N,N-bis(carboxymethyl)amine, which was prepared as described in Example 5, with the intermediate indole and subsequent reaction of the indole intermediate with glutaconaldehyde dianil monohydrochloride (see Example 1) gives the desired product. at reflux for 1
Source ID: ord-e07fbb538b0940428cdc6f57569b2167Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The hydroxy-indole compound is readily prepared by literature method (P. L. Southwick, J. G. Cairns, L. A. Ernst, and A. S. Waggoner, One pot Fischer synthesis of (2,3,3-trimethyl-3-H-indol-5-yl)-acetic acid derivatives as intermediates for fluorescent biolabels. Org. Prep. Proced. Int. Briefs, 1988, 20(3), 279-284). Reaction of p-carboxymethylphenylhydrazine hydrochloride (30 mmol, 1 equiv.) and 1,1-bis(hydroxymethyl)propanone (45 mmole, 1.5 equiv.) in acetic acid (50 mL) at room temperature for 30 minutes and at reflux for 1 gives (3,3-dihydroxymethyl2-methyl-3-H-indol-5-yl)-acetic acid as a solid residue. The reaction of 3-bromopropyl-N,N-bis(carboxymethyl)amine, which was prepared as described in Example 5, with the intermediate indole and subsequent reaction of the indole intermediate with glutaconaldehyde dianil monohydrochloride (see Example 1) gives the desired product. at reflux for 1
Source ID: ord-0ab7c9108f9643d4b3d250498017dccaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The hydroxy-indole compound is readily prepared by literature method (P. L. Southwick, J. G. Cairns, L. A. Ernst, and A. S. Waggoner, One pot Fischer synthesis of (2,3,3-trimethyl-3-H-indol-5-yl)-acetic acid derivatives as intermediates for fluorescent biolabels. Org. Prep. Proced. Int. Briefs, 1988, 20(3), 279-284). Reaction of p-carboxymethylphenylhydrazine hydrochloride (30 mmol, 1 equiv.) and 1,1-bis(hydroxymethyl)propanone (45 mmole, 1.5 equiv.) in acetic acid (50 mL) at room temperature for 30 minutes and at reflux for 1 gives (3,3-dihydroxymethyl2-methyl-3-H-indol-5-yl)-acetic acid as a solid residue. The reaction of 3-bromopropyl-N,N-bis(carboxymethyl)amine, which was prepared as described in Example 5, with the intermediate indole and subsequent reaction of the indole intermediate with glutaconaldehyde dianil monohydrochloride (see Example 1) gives the desired product. at reflux for 1
Source ID: ord-2722f5a263a2446d9cdd166a7c252f7dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The hydroxy-indole compound is readily prepared by literature method (P. L. Southwick, J. G. Cairns, L. A. Ernst, and A. S. Waggoner, One pot Fischer synthesis of (2,3,3-trimethyl-3-H-indol-5-yl)-acetic acid derivatives as intermediates for fluorescent biolabels. Org. Prep. Proced. Int. Briefs, 1988, 20(3), 279-284). Reaction of p-carboxymethylphenylhydrazine hydrochloride (30 mmol, 1 equiv.) and 1,1-bis(hydroxymethyl)propanone (45 mmole, 1.5 equiv.) in acetic acid (50 mL) at room temperature for 30 minutes and at reflux for 1 gives (3,3-dihydroxymethyl2-methyl-3-H-indol-5-yl)-acetic acid as a solid residue. The reaction of 3-bromopropyl-N,N-bis(carboxymethyl)amine, which was prepared as described in Example 5, with the intermediate indole and subsequent reaction of the indole intermediate with glutaconaldehyde dianil monohydrochloride (see Example 1) gives the desired product. at reflux for 1
Source ID: ord-c7add50c7e8a4e65992efe532f1590f7Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The hydroxy-indole compound is readily prepared by literature method (P. L. Southwick, J. G. Cairns, L. A. Ernst, and A. S. Waggoner, One pot Fischer synthesis of (2,3,3-trimethyl-3-H-indol-5-yl)-acetic acid derivatives as intermediates for fluorescent biolabels. Org. Prep. Proced. Int. Briefs, 1988, 20(3), 279-284). Reaction of p-carboxymethylphenylhydrazine hydrochloride (30 mmol, 1 equiv.) and 1,1-bis(hydroxymethyl)propanone (45 mmole, 1.5 equiv.) in acetic acid (50 mL) at room temperature for 30 minutes and at reflux for 1 gives (3,3-dihydroxymethyl2-methyl-3-H-indol-5-yl)-acetic acid as a solid residue. The reaction of 3-bromopropyl-N,N-bis(carboxymethyl)amine, which was prepared as described in Example 5, with the intermediate indole and subsequent reaction of the indole intermediate with glutaconaldehyde dianil monohydrochloride (see Example 1) gives the desired product. at reflux for 1
Source ID: ord-e02459db7e984713a08f8a1575d225d6Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The hydroxy-indole compound is readily prepared by a known method (P. L. Southwick, et al., One pot Fischer synthesis of (2,3,3-trimethyl-3-H-indol-5-yl)-acetic acid derivatives as intermediates for fluorescent biolabels. Org. Prep. Proced. Int. Briefs, 1988, 20(3), 279-284). Reaction of p-carboxymethylphenylhydrazine hydrochloride (30 mmol, 1 equiv.) and 1,1-bis(hydroxymethyl)propanone (45 mmole, 1.5 equiv.) in acetic acid (50 mL) at room temperature for 30 minutes and at reflux for one minute gives (3,3-dihydroxymethyl-2-methyl-3-H-indol-5-yl)-acetic acid as a solid residue. The reaction of 3-bromopropyl-N,N-bis(carboxymethyl)amine, which was prepared as described in Example 5, with the intermediate indole and subsequent reaction of the indole intermediate with glutaconaldehyde dianil monohydrochloride (see Example 1) gives the desired product. at reflux for one minute
Source ID: ord-6a2c87bfc5b345d5815644f5ee4b926dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The hydroxy-indole compound is readily prepared by a known method (P. L. Southwick et al., One pot Fischer synthesis of (2,3,3-trimethyl-3-H-indol-5-yl)-acetic acid derivatives as intermediates for fluorescent biolabels. Org. Prep. Proced. Int. Briefs, 1988, 20(3), 279-284). Reaction of p-carboxymethylphenylhydrazine hydrochloride (30 mmol, 1 equiv.) and 1,1-bis(hydroxymethyl)propanone (45 mmole, 1.5 equiv.) in acetic acid (50 mL) at room temperature for 30 minutes and at reflux for one minute gives (3,3-dihydroxymethyl-2-methyl-3-H-indol-5-yl)-acetic acid as a solid residue. The reaction of 3-bromopropyl-N,N-bis(carboxymethyl)amine, which was prepared as described in Example 5, with the intermediate indole and subsequent reaction of the indole intermediate with glutaconaldehyde dianil monohydrochloride (see Example 1) gives the desired product. at reflux for one minute
Source ID: ord-d34ce3ce418645179d04f6e9b992abebConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The hydroxy-indole compound is readily prepared by a known method (P. L. Southwick, et al., One pot Fischer synthesis of (2,3,3-trimethyl-3-H-indol-5-yl)-acetic acid derivatives as intermediates for fluorescent biolabels. Org. Prep. Proced. Int. Briefs, 1988, 20(3), 279-284). Reaction of p-carboxymethylphenylhydrazine hydrochloride (30 mmol, 1 equiv.) and 1,1-bis(hydroxymethyl)propanone (45 mmole, 1.5 equiv.) in acetic acid (50 mL) at room temperature for 30 minutes and at reflux for one minute gives (3,3-dihydroxymethyl-2-methyl-3-H-indol-5-yl)-acetic acid as a solid residue. The reaction of 3-bromopropyl-N,N-bis(carboxymethyl)amine, which was prepared as described in Example 5, with the intermediate indole and subsequent reaction of the indole intermediate with glutaconaldehyde dianil monohydrochloride (see Example 1) gives the desired product. at reflux for one minute
Source ID: ord-af4ec8560fa44266a6d034848aec9d1fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The hydroxyindole compound was readily prepared by a literature method (P. L. Southwick, J. G. Cairns, L. A. Ernst, and A. S. Waggoner, One pot Fischer synthesis of (2,3,3-trimethyl-3-H-indol-5-yl)-acetic acid derivatives as intermediates for fluorescent biolabels. Org. Prep. Proced. Int. Briefs, 1988, 20(3), 279-284). Reaction of p-carboxymethylphenylhydrazine hydrochloride (30 mmol, 1 equiv.) and 1,1-bis(hydroxymethyl)propanone (45 mmol, 1.5 equiv.) in acetic acid (50 mL) at room temperature for 30 minutes and at reflux for 1 gave (3,3-dihydroxymethyl2-methyl-3-H-indol-5-yl)-acetic acid as a solid residue. at reflux for 1
Source ID: ord-c8ab01d1d7a44fac840ae777571bdf65PubChem References
These sources are listed in the compound's public database record.
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