Hydroxyamine hydrochloride → HCID 73679201, compound

HRID 2418319Notes

Reaction equation

HRID 2418319 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:6]=2[CH:21]=1.Cl.[NH2:23][OH:24]>N1C=CC=CC=1.C(Cl)(Cl)Cl.C(O)C>[NH2:8][CH2:9][C:10]([N:11]([CH3:12])[C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:21][C:6]=1[C:7](=[N:23][OH:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])=[O:13]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 204463287-amino-5-(o-chlorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one

Product 1

HCID 73679201HCID 73679201, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 21889567Chloroform ethanolSolvent

Procedure

A solution of 5.0 g (16.68 mmol) of 7-amino-5-(o-chlorophenyl)-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one and 1.74 g (22.02 mmol) of hydroxylamine hydrochloride in 50 ml of pyridine is heated to reflux for 2 hours under argon. After cooling, the mixture is taken up in 600 ml chloroform/ethanol (4:1) and washed with 250 ml of water. The aqueous phase is adjusted to pH 8, saturated with sodium chloride and extracted with chloroform overnight in a perforator. After drying and evaporating the solvent, the residue is suspended in hot tert.-butyl methyl ether and filtered off. There is obtained 2,4'-diamino-2'-[o-chloro-α-(hydroxyimino)benzyl]-N-methylacetanilide of melting point 150° (decomposition).

Workup

  1. temperatureto reflux for 2 hours under argon
  2. temperatureAfter cooling
  3. washwashed with 250 ml of water
  4. extractionextracted with chloroform overnight in a perforator
  5. customAfter drying
  6. customevaporating the solvent
  7. filtrationfiltered off

Sources & evidence

ORD record
ord-a2f29453bc7c423baf3d47a96fa6d953
Source dataset
uspto-grants-1984_09
Patent number
US04472435

Reaction notes

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