Hydroxyamine hydrochloride → 5-(o-fluorophenyl)-1,3-dihydro-7-[1-(hydroxyimino)ethyl]-1,3-dimethyl-2H-1,4-benzodiazepin-2-one

HRID 2286165Notes

Reaction equation

HRID 2286165 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH3:14])[C:12](=[O:15])[CH:11]([CH3:16])[N:10]=[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[C:8]=2[CH:24]=1)(=O)[CH3:2].Cl.[NH2:26][OH:27]>N1C=CC=CC=1>[F:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:9]1[C:8]2[CH:24]=[C:4]([C:1](=[N:26][OH:27])[CH3:2])[CH:5]=[CH:6][C:7]=2[N:13]([CH3:14])[C:12](=[O:15])[CH:11]([CH3:16])[N:10]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 20542067HCID 20542067, compound

Product 1

HCID 736829855-(o-fluorophenyl)-1,3-dihydro-7-[1-(hydroxyimino)ethyl]-1,3-dimethyl-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4.41 g (13.60 mmol) of 7-acetyl-5-(o-fluorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one and 4.41 g (63.46 mmol) of hydroxylamine hydrochloride in 250 ml of pyridine is stirred at room temperature for 19 hours, subsequently poured on to ice and extracted with chloroform. The organic extracts are washed successively with 2 N hydrochloric acid and water, dried and evaporated. After chromatography of the residue on 250 g of silica gel using chloroform/ethanol (98:2) as the elution agent, there is obtained 5-(o-fluorophenyl)-1,3-dihydro-7-[1-(hydroxyimino)ethyl]-1,3-dimethyl-2H-1,4-benzodiazepin-2-one of melting point 101°-103°.

Workup

  1. additionsubsequently poured on to ice
  2. extractionextracted with chloroform
  3. washThe organic extracts are washed successively with 2 N hydrochloric acid and water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-928191d9cb1b40188b9814f9327bd5f5
Source dataset
uspto-grants-1982_04
Patent number
US04327026

Reaction notes

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