Ammonium Chloride → Benzoic acid, 4-amino-2-ethoxy-, ethyl ester

HRID 2105847Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[Cl-].[NH4+]>C(O)C.[Fe]>[NH2:15][C:13]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([O:3][CH2:1][CH3:2])[CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 2-ethoxy-4-nitro-benzoate (12.7 g, 53.1 mmol) in ethanol (94 mL) was added a solution of ammonium chloride (56 mL). The formation of a precipitate was observed. Iron (15.2 g, 271 mmol) was added and the reaction mixture was heated at 80° C. for 16 h. The reaction mixture was cooled and filtered through Celite, and the Celite was rinsed with methylene chloride. Water was added and the product was extracted three times with methylene chloride. The organic layers were dried over magnesium sulfate and concentrated. Purification of the crude residue by flash column chromatography (silica gel, eluting with 0-3% methanol in chloroform) gave ethyl 4-amino-2-ethoxy-benzoate as a tan solid (10.3 g, 99%).

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered through Celite
washthe Celite was rinsed with methylene chloride
additionWater was added
extractionthe product was extracted three times with methylene chloride
dry with materialThe organic layers were dried over magnesium sulfate
concentrationconcentrated
customPurification of the crude residue
washby flash column chromatography (silica gel, eluting with 0-3% methanol in chloroform)

Sources & evidence

ORD record: ord-affea29c0dd8472ea1abb2b1fe29e9b3
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579368B2

Reaction notes

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