Water → Ethyl 2-hydroxy-5-acetamidobenzoate

HRID 2107013Notes

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

Reactant 3

HCID 962Water

HCID 7918Acetic Anhydride

HCID 13445456Ethyl 5-amino-2-hydroxybenzoate

Product 1

HCID 23047221Ethyl 2-hydroxy-5-acetamidobenzoateYield 65%

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).

Workup

temperatureThe mixture was cooled to room temperature
customthe mixture was evaporated to dryness
customThe remaining material was recrystallized from water-ethanol (1:1)

Sources & evidence

ORD record: ord-c34d3b4b71744d1299b22c6e946f8af9
Source dataset: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04933330

Reaction notes

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