Diisopropyl Ether → Methyl 2-acetamido-3-acetoxybenzoate

HRID 278082Notes

Reaction equation

HRID 278082 reaction equation
[NH2:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13](OC(=O)C)(=[O:15])[CH3:14].[CH:20]([O:23]C(C)C)(C)[CH3:21]>N1C=CC=CC=1>[C:13]([NH:1][C:2]1[C:11]([O:12][C:20](=[O:23])[CH3:21])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 7918Acetic AnhydrideHCID 205248Anthranilic acid, 3-hydroxy-, methyl ester

Product 1

HCID 22627220Methyl 2-acetamido-3-acetoxybenzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of methyl 2-amino-3-hydroxybenzoate (882 mg) in pyridine (2 ml) was added acetic anhydride (1.2 ml) and the mixture was stirred at 20° C. for 8 hours. The reaction mixture was diluted with diisopropyl ether, and the resulting solid was collected and washed with diisopropyl ether. The solid was triturated with diisopropyl ether to give methyl 2-acetamido-3-acetoxybenzoate (1.25 g) as solid.

Workup

  1. customthe resulting solid was collected
  2. washwashed with diisopropyl ether
  3. customThe solid was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-220fb2030ea249dfb5f93ee57b7c112a
Source dataset
uspto-grants-2002_03
Patent number
US06358992B1

Reaction notes

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