No renderable structure data available
COC1=C(C=CC(=C1)N)C2CC2Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-cyclopropyl-3-methoxyaniline |
|---|---|
| IUPAC Name | — |
| CAS Number | 1233531-34-4 |
| Database ID | 59394955 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-cyclopropyl-3-methoxyaniline (CAS 1233531-34-4) 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 59394955
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-7a7ae1755ab94872baafbd25db740e3fConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-32795e8531f84d559358b0e0202c5826Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of BBr3 in dichloromethane (4.47 mL of 1M, 4.47 mmol) was added to a solution of 4-cyclopropyl-3-methoxyaniline (243 mg, 1.49 mmol) in dichloromethane (15 mL) at 0° C. under N2 atmosphere. The reaction was stirred for 30 min at 0° C. then diluted with dichloromethane (10 mL). The reaction mixture was washed with aqueous NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by HPLC (10-99% CH3CN.0.05% TFA) to provide 5-amino-2-cyclopropylphenol (115 mg, 52% yield). LC/MS m/z 150.1 [M+H]+. The reaction mixture was washed with aqueous NaHCO3, water and brine The organic layer was dried over Na2SO4 filtered concentrated in vacuo The product was purified by HPLC (10-99% CH3CN.0.05% TFA)
Source ID: ord-db370360d31a4afb82e32c5ecc8fa1f8Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4-bromo-3-methoxyaniline (1 g, 4.98 mmol) in 3:2 toluene/water (10 mL) was added cyclopropylboronic acid (514 mg, 5.98 mmol), Pd(OAc)2 (56 mg, 0.25 mmol), PCy3 (140 mg, 0.5 mmol) and K3PO4 (3.18 g, 15 mmol) at room temperature. The mixture was stirred at 100° C. for 10 h. The solid was filtered and the filtrate concentrated in vacuo. Purification by silica gel chromatography (2-10% ethyl acetate/hexanes) provided 4-cyclopropyl-3-methoxyaniline (200 mg, 25%) as a brown solid. 1H NMR (300 MHz, CDCl3) δ 6.67 (d, J=7.8 Hz, 1H), 6.24-6.20 (m, 2H), 3.82 (s, 3H), 3.50 (brs, 2H), 2.02-1.95 (m, 1H), 0.85-0.79 (m, 2H), 0.57-0.51 (m, 2H). The solid was filtered the filtrate concentrated in vacuo Purification by silica gel chromatography (2-10% ethyl acetate/hexanes)
Source ID: ord-2bcad5dfdd9b4d038e4510c051091463Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of BBr3 in dichloromethane (4.47 mL of 1 M, 4.47 mmol) was added to a solution of 4-cyclopropyl-3-methoxyaniline (243 mg, 1.49 mmol) in dichloromethane (15 mL) at 0° C. under N2 atmosphere. The reaction was stirred for 30 min at 0° C. then diluted with dichloromethane (10 mL). The reaction mixture was washed with aqueous NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by HPLC (10-99% CH3CN 0.05% TFA) to provide 5-amino-2-cyclopropylphenol (115 mg, 52% yield). LC/MS m/z 150.1 [M+H]+. The reaction mixture was washed with aqueous NaHCO3, water and brine The organic layer was dried over Na2SO4 filtered concentrated in vacuo The product was purified by HPLC (10-99% CH3CN 0.05% TFA)
Source ID: ord-6f6f9cd66a164c26bc5edcbbc8c04c4bConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of BBr3 in dichloromethane (4.47 mL of 1 M, 4.47 mmol) was added to a solution of 4-cyclopropyl-3-methoxyaniline (243 mg, 1.49 mmol) in dichloromethane (15 mL) at 0° C. under N2 atmosphere. The reaction was stirred for 30 min at 0° C. then diluted with dichloromethane (10 mL). The reaction mixture was washed with aqueous NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by HPLC (10-99% CH3CN 0.05% TFA) to provide 5-amino-2-cyclopropylphenol (115 mg, 52% yield). LC/MS m/z 150.1 [M+H]+. The reaction mixture was washed with aqueous NaHCO3, water and brine The organic layer was dried over Na2SO4 filtered concentrated in vacuo The product was purified by HPLC (10-99% CH3CN 0.05% TFA)
Source ID: ord-6f6f9cd66a164c26bc5edcbbc8c04c4bConditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4-bromo-3-methoxyaniline (1 g, 4.98 mmol) in 3:2 toluene/water (10 mL) was added cyclopropylboronic acid (514 mg, 5.98 mmol), Pd(OAc)2 (56 mg, 0.25 mmol), PCy3 (140 mg, 0.5 mmol) and K3PO4 (3.18 g, 15 mmol) at room temperature. The mixture was stirred at 100° C. for 10 h. The solid was filtered and the filtrate concentrated in vacuo. Purification by silica gel chromatography (2-10% ethyl acetate/hexanes) provided 4-cyclopropyl-3-methoxyaniline (200 mg, 25%) as a brown solid. 1H NMR (300 MHz, CDCl3) 6.67 (d, J=7.8 Hz, 1H), 6.24-6.20 (m, 2H), 3.82 (s, 3H), 3.50 (brs, 2H), 2.02-1.95 (m, 1H), 0.85-0.79 (m, 2H), 0.57-0.51 (m, 2H). The solid was filtered the filtrate concentrated in vacuo Purification by silica gel chromatography (2-10% ethyl acetate/hexanes)
Source ID: ord-929b6441b29943cbab441d7158e13001Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of BBr3 in dichloromethane (4.47 mL of 1M, 4.47 mmol) was added to a solution of 4-cyclopropyl-3-methoxyaniline (243 mg, 1.49 mmol) in dichloromethane (15 mL) at 0° C. under N2 atmosphere. The reaction was stirred for 30 min at 0° C. then diluted with dichloromethane (10 mL). The reaction mixture was washed with aqueous NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by HPLC (10-99% CH3CN.0.05% TFA) to provide 5-amino-2-cyclopropylphenol (115 mg, 52% yield). LC/MS m/z 150.1 [M+H]+. The reaction mixture was washed with aqueous NaHCO3, water and brine The organic layer was dried over Na2SO4 filtered concentrated in vacuo The product was purified by HPLC (10-99% CH3CN.0.05% TFA)
Source ID: ord-db370360d31a4afb82e32c5ecc8fa1f8Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of BBr3 in dichloromethane (4.47 mL of 1M, 4.47 mmol) was added to a solution of 4-cyclopropyl-3-methoxyaniline (243 mg, 1.49 mmol) in dichloromethane (15 mL) at 0° C. under N2 atmosphere. The reaction was stirred for 30 min at 0° C. then diluted with dichloromethane (10 mL). The reaction mixture was washed with aqueous NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by HPLC (10-99% CH3CN.0.05% TFA) to provide 5-amino-2-cyclopropylphenol (115 mg, 52% yield). LC/MS m/z 150.1 [M+H]+. The reaction mixture was washed with aqueous NaHCO3, water and brine The organic layer was dried over Na2SO4 filtered concentrated in vacuo The product was purified by HPLC (10-99% CH3CN.0.05% TFA)
Source ID: ord-db370360d31a4afb82e32c5ecc8fa1f8Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a stirred solution of 4-bromo-3-methoxyaniline (1 g, 4.98 mmol) in 3:2 toluene/water (10 mL) was added cyclopropylboronic acid (514 mg, 5.98 mmol), Pd(OAc)2 (56 mg, 0.25 mmol), PCy3 (140 mg, 0.5 mmol) and K3PO4 (3.18 g, 15 mmol) at room temperature. The mixture was stirred at 100° C. for 10 h. The solid was filtered and the filtrate concentrated in vacuo. Purification by silica gel chromatography (2-10% ethyl acetate/hexanes) provided 4-cyclopropyl-3-methoxyaniline (200 mg, 25%) as a brown solid. 1H NMR (300 MHz, CDCl3) δ 6.67 (d, J=7.8 Hz, 1H), 6.24-6.20 (m, 2H), 3.82 (s, 3H), 3.50 (brs, 2H), 2.02-1.95 (m, 1H), 0.85-0.79 (m, 2H), 0.57-0.51 (m, 2H). The solid was filtered the filtrate concentrated in vacuo Purification by silica gel chromatography (2-10% ethyl acetate/hexanes)
Source ID: ord-2bcad5dfdd9b4d038e4510c051091463Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-7a7ae1755ab94872baafbd25db740e3fConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of BBr3 in dichloromethane (4.47 mL of 1 M, 4.47 mmol) was added to a solution of 4-cyclopropyl-3-methoxyaniline (243 mg, 1.49 mmol) in dichloromethane (15 mL) at 0° C. under N2 atmosphere. The reaction was stirred for 30 min at 0° C. then diluted with dichloromethane (10 mL). The reaction mixture was washed with aqueous NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The product was purified by HPLC (10-99% CH3CN. 0.05% TFA) to provide 5-amino-2-cyclopropylphenol (115 mg, 52% yield). LC/MS m/z 150.1 [M+H]+. The reaction mixture was washed with aqueous NaHCO3, water and brine The organic layer was dried over Na2SO4 filtered concentrated in vacuo The product was purified by HPLC (10-99% CH3CN. 0.05% TFA)
Source ID: ord-c203bf277e3a491daee705e39efeb3cePubChem References
These sources are listed in the compound's public database record.
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