Water → Methyl 4-acetamidosalicylate

HRID 2107019Notes

Reaction equation

HRID 2107019 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([NH2:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].O.[C:14](OC(=O)C)(=[O:16])[CH3:15]>>[OH:1][C:2]1[CH:11]=[C:10]([NH:12][C:14](=[O:16])[CH3:15])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 77787Methyl p-aminosalicylate

Product 1

HCID 77719Methyl 4-acetamidosalicylateYield 70%

Conditions

Temperature
75 °C

Procedure

Methyl 2-hydroxy-4-aminobenzoate (5.0 g, 30 mmole) was dissolved in acetic anhydride (30 ml) and heated to 75° C. for 5 minutes, after which it was cooled, water (50 ml) was added, and the reaction mixture was evaporated to dryness, in vacuo. The product was recrystallized from water to give the title compound (1.25 g, 70%), m.p. 148°-151° C. Found (Calc. for C10H11NO4) C 57.53 (57.01), H 5.33 (5.27), N 6.68 (6.70).

Workup

  1. temperatureafter which it was cooled
  2. customthe reaction mixture was evaporated to dryness, in vacuo
  3. customThe product was recrystallized from water

Sources & evidence

ORD record
ord-1a47edd6f76c469995a532115e7fa1d0
Source dataset
uspto-grants-1990_06
Patent number
US04933330

Reaction notes

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