Nitrazepam → 2-Amino-2'-[alpha-(hydroxyimino)benzyl]-4'-nitro-acetanilide

HRID 2418314

Reaction equation

HRID 2418314 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:13][C:12](=[O:14])[CH2:11][N:10]=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[CH:21]=1)([O-:3])=[O:2].Cl.[NH2:23][OH:24]>N1C=CC=CC=1.C(Cl)Cl>[NH2:10][CH2:11][C:12]([NH:13][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:21][C:8]=1[C:9](=[N:23][OH:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14]

Participants

5

Reactant 2

HCID 4506NitrazepamHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 867396452-Amino-2'-[alpha-(hydroxyimino)benzyl]-4'-nitro-acetanilide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 10 g (35.55 mmol) of 1,3-dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one and 3.7 g (53.3 mmol) of hydroxylamine hydrochloride in 80 ml of pyridine is heated under reflux for 1 hour. After cooling, the mixture is taken up in methylene chloride, washed with water, dried and evaporated. The residual pyridine is removed in vacuo azeotropically with toluene. The solid crude product is suspended in hot tert.-butyl methyl ether and filtered off. There is obtained 2-amino-2'-[α-(hydroxyimino)-benzyl]-4'-nitro-acetanilide of melting point 167° (decomposition).

Workup

  1. temperatureunder reflux for 1 hour
  2. temperatureAfter cooling
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customThe residual pyridine is removed in vacuo azeotropically with toluene
  7. filtrationfiltered off

Sources & evidence

ORD record
ord-c547788ae59b419babdca8db616cd6d3
Source dataset
uspto-grants-1984_09
Patent number
US04472435

Linked notes

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