No renderable structure data available
COC(=O)C1=CC2=C(N1)C=CC=C2OChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | methyl 4-hydroxy-1H-indole-2-carboxylate |
|---|---|
| IUPAC Name | — |
| CAS Number | 27748-08-9 |
| Database ID | 22310940 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
methyl 4-hydroxy-1H-indole-2-carboxylate (CAS 27748-08-9) 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 22310940
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-338c5a1d9a3e43f69663c57a0ad96cdfConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-53c9ec0256b94891b7d0fc2a4d285d79Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Boron tribromide (73.1 ml, 1.0 M solution in DCM) was added dropwise to a solution of methyl 4-methoxyindole-2-carboxylate (5 g) in DCM (200 ml) cooled to −78° C. under argon. The reaction was allowed to warm to room temperature then partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate solution. Combined organic extracts were dried (MgSO4) and concentrated in vacuo and the residue purified by column chromatography using iso-hexane-50% ethyl acetate as eluent to give the end product as a yellow solid (2.98 g, 64%); NMR d (CD3SOCD3) 3.82 (s, 3H), 6.36 (d, 1H), 6.85 (d, 1H), 7.02 (t, 1H), 7.17 (d, 1H), 9.66 (s, 1H), 11.72 (bs, 1H); M/z (+) 192 (MH+). to warm to room temperature then partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate solution Combined organic extracts were dried (MgSO4) concentrated in vacuo the residue purified by column chromatography
Source ID: ord-4d86c6be9e2e4c869fb3a2a0d5b2fa61Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-338c5a1d9a3e43f69663c57a0ad96cdfConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Methyl 4-hydroxyindole-2-carboxylate (0.5 g) and 4-dimethylaminopyridine (50 mg) were dissolved in acetic anhydride (5 ml) and heated at 80° C. for 3 hours. The reaction was allowed to cool overnight to precipitate white crystals, which were filtered and dried in vacuo (0.44 g, 72%); NMR δ (CD3SOCD3) 2.34 (s, 3H), 3.85 (s, 3H), 6.80 (d, 1H), 7.06 (s, 1H), 7.23 (t, 1H), 7.29-7.35 (m, 1H), 12.1 (bs, 1H); M/z (−) 232 (M−H+). to cool overnight to precipitate white crystals, which were filtered dried in vacuo (0.44 g, 72%)
Source ID: ord-91fcb033532a4634b61fc9e69f0abe6fConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Boron tribromide (73.1 ml, 1.0 M solution in DCM) was added dropwise to a solution of methyl 4-methoxyindole-carboxylate (5 g) in DCM (200 ml) cooled to −78° C. under argon. The reaction was allowed to warm to room temperature then partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate solution. Combined organic extracts were dried (MgSO4) and concentrated in vacuo and the residue purified by column chromatography using isohexane-50% ethyl acetate as eluent to give the end product as a yellow solid (2.98 g, 64%); NMR δ (CD3SOCD3) 3.82 (s, 3H), 6.36 (d, 1H), 6.85 (d, 1H), 7.02 (t, 1H), 7.17 (d, 11H), 9.66 (s, 1H), 11.72 (bs, 11H); M/z (+) 192 (MH+). to warm to room temperature then partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate solution Combined organic extracts were dried (MgSO4) concentrated in vacuo the residue purified by column chromatography
Source ID: ord-0fd17adb8e6648a994e3258094c8193dConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Boron tribromide (73.1 ml, 1.0 M solution in DCM) was added dropwise to a solution of methyl 4-methoxyindole-carboxylate (5 g) in DCM (200 ml) cooled to −78° C. under argon. The reaction was allowed to warm to room temperature then partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate solution. Combined organic extracts were dried (MgSO4) and concentrated in vacuo and the residue purified by column chromatography using isohexane-50% ethyl acetate as eluent to give the end product as a yellow solid (2.98 g, 64%); NMR δ (CD3SOCD3) 3.82 (s, 3H), 6.36 (d, 1H), 6.85 (d, 1H), 7.02 (t, 1H), 7.17 (d, 11H), 9.66 (s, 1H), 11.72 (bs, 11H); M/z (+) 192 (MH+). to warm to room temperature then partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate solution Combined organic extracts were dried (MgSO4) concentrated in vacuo the residue purified by column chromatography
Source ID: ord-0fd17adb8e6648a994e3258094c8193dConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Boron tribromide (73.1 ml, 1.0 M solution in DCM) was added dropwise to a solution of methyl 4-methoxyindole-2-carboxylate (5 g) in DCM (200 ml) cooled to −78° C. under argon. The reaction was allowed to warm to room temperature then partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate solution. Combined organic extracts were dried (MgSO4) and concentrated in vacuo and the residue purified by column chromatography using iso-hexane-50% ethyl acetate as eluent to give the end product as a yellow solid (2.98 g, 64%); NMR d (CD3SOCD3) 3.82 (s, 3H), 6.36 (d, 1H), 6.85 (d, 1H), 7.02 (t, 1H), 7.17 (d, 1H), 9.66 (s, 1H), 11.72 (bs, 1H); M/z (+) 192 (MH+). to warm to room temperature then partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate solution Combined organic extracts were dried (MgSO4) concentrated in vacuo the residue purified by column chromatography
Source ID: ord-4d86c6be9e2e4c869fb3a2a0d5b2fa61Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-53c9ec0256b94891b7d0fc2a4d285d79Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Methyl 4-hydroxyindole-2-carboxylate (0.5 g) and 4-dimethylaminopyridine (50 mg) were dissolved in acetic anhydride (5 ml) and heated at 80° C. for 3 hours. The reaction was allowed to cool overnight to precipitate white crystals, which were filtered and dried in vacuo (0.44 g, 72%); NMR δ(CD3SOCD3) 2.34 (s, 3H), 3.85 (s, 3H), 6.80 (d, 1H) 7.06 (s, 1H), 7.23 (t, 1H), 7.29-7.35 (m, 1H), 12.1 (bs, 1H); M/z (−) 232 (M−H+). to cool overnight to precipitate white crystals, which were filtered dried in vacuo (0.44 g, 72%)
Source ID: ord-8bc9d93077464320a01e9aaf31c74108Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Boron tribromide (73.1 ml, 1.0 M solution in DCM) was added dropwise to a solution of methyl 4-methoxyindole-2carboxylate (5 g) in DCM (200 ml) cooled to −78° C. under argon. The reaction was allowed to warm to room temperature then partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate solution. Combined organic extracts were dried (MgSO4) and concentrated in vacuo and the residue purified by column chromatography using isohexane-50% ethyl acetate as eluent to give the end product as a yellow solid (2.98 g, 64%); NMR δ(CD3SOCD3) 3.82 (s, 3H), 6.36 (d, 1H), 6.85 (d, 1H), 7.02 (t, 1H), 7.17 (d, 1H), 9.66 (s, 1H), 11.72 (bs, 1H); M/z (+) 192 (MH+). to warm to room temperature then partitioned between dichloromethane and saturated aqueous sodium hydrogen carbonate solution Combined organic extracts were dried (MgSO4) concentrated in vacuo the residue purified by column chromatography
Source ID: ord-184a28488f394afeba36aa637e07b0d0Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: DEAD (0.414 ml, 2.66 mmol) is slowly added to a solution of 4-Hydroxy-1H-indole-2-carboxylic acid methyl ester 75 (363 mg, 1.9 mmol), triphenylphosphine (698 mg, 2.66 mmol) and 2,2-Dimethyl-propan-1-ol (228 mg, 2.58 mmol) in 8 ml of THF. Stirring is continued for 20 hours and the solvent is then evaporated. The crude mixture is purified by chromatography on silicagel using cyclohexane/EtOAc (9/1). the solvent is then evaporated The crude mixture is purified by chromatography on silicagel
Source ID: ord-42db2a0615d2496082b1fd0fe0e5a963PubChem References
These sources are listed in the compound's public database record.
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