4-Nitrobenzoyl chloride → Ethyl 2-amino-2-(4-nitrobenzoyloxyimino)acetate

HRID 54535

Reaction equation

HRID 54535 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:13][C:14](=[N:20][OH:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16]>O1CCCC1>[NH2:13][C:14](=[N:20][O:21][C:8](=[O:9])[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 6785548Ethyl 2-amino-2-(hydroxyimino)acetate

Product 1

HCID 53689516Ethyl 2-amino-2-(4-nitrobenzoyloxyimino)acetateYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-nitrobenzoyl chloride (10 g) in tetrahydrofuran (150 ml) was added a suspension of ethyl 2-amino-2-hydroxyiminoacetate (7.1 g) in tetrahydrofuran (30 ml). After stirring for 2 hours, the precipitates were collected by filtration and washed with diethyl ether to afford ethyl 2-amino-2-(4-nitrobenzoyloxyimino)acetate (12.19 g).

Workup

  1. filtrationthe precipitates were collected by filtration
  2. washwashed with diethyl ether

Sources & evidence

ORD record
ord-eb2980772efc4544af937d3ef0d335a3
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Linked notes

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