Ethyl 3-(2-benzoyl-4-chloroanilino)-3-oxopropanoate → Ethyl 2'-benzoyl-4'-chloro-mesoxalanilate 2-oxime

HRID 328482Notes

Reaction equation

HRID 328482 reaction equation
[N:1]([O-:3])=O.[Na+].[C:5]([C:13]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:14]=1[NH:15][C:16](=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(O)(=O)C>[C:5]([C:13]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:14]=1[NH:15][C:16](=[O:23])[C:17](=[N:1][OH:3])[C:18]([O:20][CH2:21][CH3:22])=[O:19])(=[O:12])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 21409980Ethyl 3-(2-benzoyl-4-chloroanilino)-3-oxopropanoateHCID 23668193Sodium Nitrite

Product 1

HCID 86733591Ethyl 2'-benzoyl-4'-chloro-mesoxalanilate 2-oxime

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 50 g. of sodium nitrite is added dropwise to a solution of 34.6 g. of ethyl 2'-benzoyl-4'-chloro-malonanilate in 250 ml. of glacial acetic acid. After 1 1/2 hours stirring at room temperature, the oxime crystallizes out and is filtered off by suction, washed with water and dried in vacuum. Ethyl 2'-benzoyl-4'-chloro-mesoxalanilate 2-oxime, m.p. 98°-105° is obtained.

Workup

  1. customthe oxime crystallizes out
  2. filtrationis filtered off by suction
  3. washwashed with water
  4. customdried in vacuum

Sources & evidence

ORD record
ord-0a0c3f4fbc0f4a1aa5e963b306d57197
Source dataset
uspto-grants-1977_04
Patent number
US04017531

Reaction notes

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