Hydroxyamine hydrochloride → (+/-)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carbamidoxime

HRID 25060

Reaction equation

HRID 25060 reaction equation
[CH3:1][CH:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)=[N:4][N:3]1[C:25]#[N:26].C([O-])(=O)C.[Na+].Cl.[NH2:33][OH:34]>COCCO>[CH3:1][CH:2]1[CH2:8][C:7]2[CH:9]=[C:10]3[O:15][CH2:14][O:13][C:11]3=[CH:12][C:6]=2[C:5]([C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)=[N:4][N:3]1[C:25](=[N:33][OH:34])[NH2:26]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 12137416(+/-)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carbonitrile

Product 1

HCID 86593811(+/-)-8-Methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-7-carbamidoximeYield 100%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 2.80 g (8.0 mmol) of compound XXIII, 30 ml of 2-methoxyethanol, 0.84 g (10 mmol) of sodium acetate and 0.60 g (8.8 mmol) of hydroxylamine hydrochloride was stirred for 0.5 h, then concentrated in vacuum. The residue was treated with water, the precipitated crystals were filtered off and washed with water to yield 3.05 g (100%) of the title compound, Mp.: 138-145° C.

Workup

  1. concentrationconcentrated in vacuum
  2. additionThe residue was treated with water
  3. filtrationthe precipitated crystals were filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-efa50049c5f44d9abee0181d07a2c0d7
Source dataset
uspto-grants-2005_02
Patent number
US06858605B2

Linked notes

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