Acetic Acid → Methyl 4-acetamido-5-chloro-2-methoxybenzoate

HRID 5878Notes

Reaction equation

HRID 5878 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([NH2:13])[C:10]([Cl:14])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].[C:15](O)(=[O:17])[CH3:16]>C(OC(=O)C)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]([NH:13][C:15](=[O:17])[CH3:16])[C:10]([Cl:14])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 700493Methyl 4-amino-5-chloro-2-methoxybenzoate

Product 1

HCID 77721Methyl 4-acetamido-5-chloro-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 21 g of methyl 2-methoxy-4-amino-5-chlorobenzoate is stirred in 12 ml acetic anhydride and 100 ml acetic acid at 100° C. for 24 hours. The reaction mixture is filtered, diluted with water, filtered and evaporated to dryness to obtain methyl 2-methoxy-4-acetylamino-5-chlorobenzoate which is used directly in the next step.

Workup

  1. filtrationThe reaction mixture is filtered
  2. additiondiluted with water
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-43ac3093e75347328275d77d7718f91d
Source dataset
uspto-grants-1993_09
Patent number
US05246942

Reaction notes

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