Acetic Anhydride → Methyl 2-acetamido-3-(cyclopentyloxy)-4-methoxybenzoate

HRID 2381057Notes

Reaction equation

HRID 2381057 reaction equation
[NH2:1][C:2]1[C:11]([O:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:10]([O:18][CH3:19])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:20](OC(=O)C)(=[O:22])[CH3:21].O1CCOCC1>O>[C:20]([NH:1][C:2]1[C:11]([O:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)=[C:10]([O:18][CH3:19])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 312751,4-DioxaneHCID 66781747Methyl 2-amino-3-(cyclopentyloxy)-4-methoxybenzoate

Product 1

HCID 66781936Methyl 2-acetamido-3-(cyclopentyloxy)-4-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 2-amino-3-(cyclopentyloxy)-4-methoxybenzoate (5.54 g, 20.9 mmol), acetic anhydride (21.0 mL, 222 mmol), and dioxane (35 mL) was heated at 40° C. under N2 for 17 h and then allowed to cool to rt. Water (10 mL) was added, and after 15 min of stirring, the reaction was concentrated to give methyl 2-acetamido-3-(cyclopentyloxy)-4-methoxybenzoate: MS (ESI): 307.9.

Workup

  1. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-8cff312a7f374d478dcca02f8464641e
Source dataset
uspto-grants-2012_09
Patent number
US08258154B2

Reaction notes

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