Hydrochloric Acid → Ethyl 3-nitro-4-valerylaminobenzoate

HRID 1586801Notes

Reaction equation

[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[C:16](Cl)(=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20].Cl>CN(C)C1C=CC=CC=1>[N+:13]([C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[NH:1][C:16](=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20])[C:6]([O:8][CH2:9][CH3:10])=[O:7])([O-:15])=[O:14]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of ethyl 4-amino-3-nitrobenzoate (49.5 g) and N,N-dimethylaniline (90 ml) was heated at 110° C. under nitrogen atmosphere. To the solution was added valeryl chloride (29 ml) and the mixture was stirred at 110° C. for 1.5 hours. After being cooled to room temperature, 1N hydrochloric acid was added until pH 2~3 to the reaction mixture. The aqueous solution was extracted with ethyl acetate. The organic layer was separated and washed successively with water and brine. The solution was dried over magnesium sulfate and the solvent was evaporated in vacuo. The residue was purified with silica gel column chromatography (ethyl acetate: n-hexane =1:5) to give ethyl 3-nitro-4-valerylaminobenzoate (67.5 g).

Workup

temperatureAfter being cooled to room temperature
extractionThe aqueous solution was extracted with ethyl acetate
customThe organic layer was separated
washwashed successively with water and brine
dry with materialThe solution was dried over magnesium sulfate
customthe solvent was evaporated in vacuo
customThe residue was purified with silica gel column chromatography (ethyl acetate: n-hexane =1:5)

Sources & evidence

ORD record: ord-9d8010e9699242a5b22996f0532b6521
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05215994

Reaction notes

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