Acetic Anhydride → methyl 5-acetamido-2-hydroxybenzoate

HRID 2107007Notes

Reaction equation

HRID 2107007 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13](OC(=O)C)(=[O:15])[CH3:14]>>[OH:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 135127Methyl 5-amino-2-hydroxybenzoate

Product 1

HCID 2361132methyl 5-acetamido-2-hydroxybenzoateYield 74%

Conditions

Temperature
100 °C

Procedure

Methyl 2-hydroxy-5-aminobenzoate (10 g, 60 mmole) was mixed with acetic anhydride (10 ml) and heated with stirring to 100° C. for 5 minutes. Subsequently the reaction mixture was cooled and concentrated to dryness, in vacuo. The remaining material was recrystallized from ethanol-water (1:1) with activated carbon, to give the title compound (9.7 g, 74%), m.p. 147°-148° C. Found (Calc. for C10H11NO4) C 57.01 (57.42), H 5.27 (5.26), N 6.76 (6.70).

Workup

  1. temperatureheated
  2. temperatureSubsequently the reaction mixture was cooled
  3. concentrationconcentrated to dryness, in vacuo
  4. customThe remaining material was recrystallized from ethanol-water (1:1) with activated carbon

Sources & evidence

ORD record
ord-b9eb12779b2041ce8bc7e82ccae2d833
Source dataset
uspto-grants-1990_06
Patent number
US04933330

Reaction notes

Loading…