Ethanol → Ethyl 4-amino-2-ethoxy-5-nitro-benzoate

HRID 1406541Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[K+].[NH2:11][C:12]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14](F)[CH:13]=1.[CH2:27]([OH:29])[CH3:28].ClCCl>C1COCC1>[NH2:11][C:12]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([O:29][CH2:27][CH3:28])[CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

KHMDS (1.92 g, 9.64 mmol) was added to a mixture of ethyl 4-amino-2-fluoro-5-nitro-benzoate (2.00 g, 8.77 mmol) and ethanol (0.56 mL, 9.64 mmol) in 70 mL THF at 0° C. The mixture was stirred at 60° C. for 16 h. Then KHMDS (1.92 g, 9.64 mmol) and ethanol (1.2 mL, 20.7 mmol) were added at ambient temperature and the mixture was stirred at 60° C. for 2 h. 100 mL dichloromethane were added and the mixture extracted with sat. NH4Cl (aq). The organic layer was evaporated, the residue mixed with ethyl acetate, washed with sat. NaCl (aq), dried over Na2SO4, filtered and evaporated. The residue was purified twice by chromatography (silica gel; eluens: petrol ether/ethyl acetate=1:1 and 2:1).

Workup

stirringthe mixture was stirred at 60° C. for 2 h
extractionthe mixture extracted with sat. NH4Cl (aq)
customThe organic layer was evaporated
additionthe residue mixed with ethyl acetate
washwashed with sat. NaCl (aq)
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated
customThe residue was purified twice by chromatography (silica gel; eluens: petrol ether/ethyl acetate=1:1 and 2:1)

Sources & evidence

ORD record: ord-fb248388f9c54bc8ba9663aaa49a0ced
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916599B2

Reaction notes

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