Water → Ethyl 2-hydroxy-5-acetamidobenzoate
Reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].O.[C:15](OC(=O)C)(=[O:17])[CH3:16]>>[OH:1][C:2]1[CH:12]=[CH:11][C:10]([NH:13][C:15](=[O:17])[CH3:16])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]Participants
4
Conditions
- Temperature
- 100 °C
Procedure
Ethyl 2-hydroxy-5-aminobenzoate (33.0 g, 0.182 mole) was dissolved in acetic anhydride (33 ml) and heated to 100° C. for 10 minutes. The mixture was cooled to room temperature, water (33 ml) was added and the mixture was evaporated to dryness. The remaining material was recrystallized from water-ethanol (1:1) to give the title compound (26.4 g, 65%), m.p. 135°-136° C. Found (Calc. for C11H13NO4) C 59.12 (59.19), H 5.93 (5.83), N 6.30 (6.28).