Diisopropyl Ether → Methyl 2-acetamido-3-acetoxybenzoate

HRID 1108696Notes

Reaction equation

HRID 1108696 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 18 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-cff4ce7c76cf4662b6f8a8837724d950
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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