Ethanol → 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime

HRID 1731515Notes

Reaction equation

HRID 1731515 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][N:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10](=[O:17])[N:9]([CH3:18])[CH2:8][C:7]=12)#[N:2].Cl.[NH2:20][OH:21].C(O)C.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:18][N:9]1[C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:6]2[CH:5]=[N:4][C:3]([C:1](=[N:20][OH:21])[NH2:2])=[C:7]2[CH2:8]1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 139845425-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile

Product 1

HCID 566103035,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.0125 mole 3-cyano-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine (prepared as in U.S. Pat. No. 4,316,839), 1.1 g of hydroxylamine hydrochloride, 200 ml of 99% ethanol and 5.2 ml of 20% potassium carbonate solution in water was heated with stirring for two hours. The reaction mixture was filtered and the filtrate was concentrated. The residue was treated with 100 ml of water and the crystalline solid was filtered off and washed with water.

Workup

  1. customprepared as in U.S
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. additionThe residue was treated with 100 ml of water
  5. filtrationthe crystalline solid was filtered off
  6. washwashed with water

Sources & evidence

ORD record
ord-3bf3b4cf87374648a0a3a543a506d24c
Source dataset
uspto-grants-1986_11
Patent number
US04622321

Reaction notes

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