Hydroxyamine hydrochloride → HCID 73682984, compound

HRID 2286168Notes

Reaction equation

HRID 2286168 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH2:14][CH3:15])[C:12](=[O:16])[CH2:11][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.C(O)C.C(Cl)Cl>[CH2:14]([N:13]1[C:7]2[CH:6]=[CH:5][C:4]([C:1](=[N:26][OH:27])[CH3:2])=[CH:24][C:8]=2[C:9]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])=[N:10][CH2:11][C:12]1=[O:16])[CH3:15]

Participants

6

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 20542077HCID 20542077, compound

Product 1

HCID 73682984HCID 73682984, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 13.0 g (40.1 mmol) of 7-acetyl-1-ethyl-5-(o-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one and 13.0 g of hydroxylamine hydrochloride in 65 ml of pyridine and 65 ml of ethanol is left to stand at room temperature for 4 hours. The mixture is taken up in methylene chloride, washed with 2 N hydrochloric acid and water, dried and evaporated. Traces of pyridine are removed by azeotropic evaporation with toluene. The residue gives, from methylene chloride/hexane, 1-ethyl-5-(o-fluorophenyl)-1,3-dihydro-7-[1-(hydroxyimino)ethyl]-2H-1,4-benzodiazepin-2-one of melting point 236°-238°.

Workup

  1. washwashed with 2 N hydrochloric acid and water
  2. customdried
  3. customevaporated
  4. customTraces of pyridine are removed by azeotropic evaporation with toluene

Sources & evidence

ORD record
ord-83db39a561e343e4855e834f21fc95d9
Source dataset
uspto-grants-1982_04
Patent number
US04327026

Reaction notes

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