Hydroxyamine hydrochloride → HCID 86738350, compound

HRID 2286175Notes

Reaction equation

HRID 2286175 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH3:14])[C:12](=[O:15])[C:11]([CH3:17])([CH3:16])[N:10]=[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[C:8]=2[CH:25]=1)(=O)[CH3:2].Cl.[NH2:27][OH:28]>N1C=CC=CC=1>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:9]1[C:8]2[CH:25]=[C:4]([C:1](=[N:27][OH:28])[CH3:2])[CH:5]=[CH:6][C:7]=2[N:13]([CH3:14])[C:12](=[O:15])[C:11]([CH3:17])([CH3:16])[N:10]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 20542068HCID 20542068, compound

Product 1

HCID 86738350HCID 86738350, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 13.66 g (40.37 mmol) of 7-acetyl-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one and 13.6 g (0.196 mol) of hydroxylamine hydrochloride in 50 ml of pyridine is stirred at room temperature for 18 hours, then poured on to ice and extracted with methylene chloride/ethanol (9:1). The organic phase is washed successively with 3 N hydrochloric acid and water, dried and evaporated. The residue is chromatographed on 150 g of silica gel using methylene chloride as the elution agent and there is obtained, from ether, 5-(o-fluorophenyl)-1,3-dihydro-7-[1-(hydroxyimino)-ethyl]-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one of melting point 199°.

Workup

  1. additionpoured on to ice
  2. extractionextracted with methylene chloride/ethanol (9:1)
  3. washThe organic phase is washed successively with 3 N hydrochloric acid and water
  4. customdried
  5. customevaporated
  6. customThe residue is chromatographed on 150 g of silica gel

Sources & evidence

ORD record
ord-10d9447a2bb04307a0c62eda090d91e8
Source dataset
uspto-grants-1982_04
Patent number
US04327026

Reaction notes

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