Hydrazine hydrate (1:1) → 5H-2,3-Benzodiazepine-4-methanol, 1-(3-chlorophenyl)-7,8-dimethoxy-

HRID 1590591Notes

Reaction equation

HRID 1590591 reaction equation
C([O:4][CH2:5][C:6](=O)[CH2:7][C:8]1[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[CH:19][C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=1)=O)(=O)C.O.[NH2:29][NH2:30]>C(O)C>[Cl:18][C:14]1[CH:13]=[C:12]([C:10]2[C:9]3[CH:19]=[C:20]([O:25][CH3:26])[C:21]([O:23][CH3:24])=[CH:22][C:8]=3[CH2:7][C:6]([CH2:5][OH:4])=[N:30][N:29]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 19767597HCID 19767597, compound

Product 1

HCID 30725215H-2,3-Benzodiazepine-4-methanol, 1-(3-chlorophenyl)-7,8-dimethoxy-Yield 77.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.7 g (17.3 mmoles) of 2-(3-acetoxyacetonyl)-3'-chloro-4,5-dimethoxybenzophenone [(IV), R=CH3 ] are suspended in 70 ml of 99.5% ethanol, then 5.2 l (104 mmoles) of 100% hydrazine hydrate are added under stirring. The reaction mixture is stirred at room temperature for 72 hours, treated with activated carbon, filtered and 82 ml of distilled water are added to the filtrate. Then 4 ml of glacial acetic acid are dropped to the pale yellow solution under cooling with ice-cold water. Upon scratching crystals get separated. The suspension is kept overnight at 1° to 5° C., filtered, washed five times with 5 ml of ice-cold 50% ethanol solution each and the product is dried at a temperature between 80° and 100° C. Thus 4.64 g of crude product are obtained.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 72 hours
  2. additiontreated with activated carbon
  3. filtrationfiltered
  4. addition82 ml of distilled water are added to the filtrate
  5. additionThen 4 ml of glacial acetic acid are dropped to the pale yellow solution
  6. temperatureunder cooling with ice-cold water
  7. customget
  8. customseparated
  9. filtrationfiltered
  10. washwashed five times with 5 ml of ice-cold 50% ethanol solution each and the product
  11. customis dried at a temperature between 80° and 100° C

Sources & evidence

ORD record
ord-cedc4af10ef64403a3d211cd197edeea
Source dataset
uspto-grants-1993_04
Patent number
US05204343

Reaction notes

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