Acetic Acid → 5,10-Dihydro-5-(4-amino-2-chlorobenzoyl)-4H-pyrazolo[5,1-c][1,4]benzodiazepine

HRID 440029Notes

Reaction equation

HRID 440029 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[N:21]=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[C:6]([Cl:26])[CH:5]=1)([O-])=O.C([O-])(O)=O.[Na+].C(O)(=O)C>C(O)C>[NH2:1][C:4]1[CH:25]=[CH:24][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[N:21]=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])=[C:6]([Cl:26])[CH:5]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 218371185,10-dihydro-5-(4-nitro-2-chlorobenzoyl)-4H-pyrazolo[5,1-c](1,4]benzodiazepine

Product 1

HCID 218369655,10-Dihydro-5-(4-amino-2-chlorobenzoyl)-4H-pyrazolo[5,1-c][1,4]benzodiazepineYield 78.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.553 g of 5,10-dihydro-5-(4-nitro-2-chlorobenzoyl)-4H-pyrazolo[5,1-c][1,4]benzodiazepine, 1.70 g of stannous chloride dihydrate in 20 ml of ethanol is heated at 70°-80° C. for 1 hour. The mixture is chilled, made basic with 1M NaHCO3 and then stirred at room temperature for 0.5 hour. The mixture is brought to pH 5 with acetic acid and extracted (several times) with ethyl acetate. The combined extracts are dried Na2SO4) and passed through a pad of hydrous magnesium silicate. The filtrate is evaporated and the residue dissolved in dichloromethane and the solution passed through a thin pad of hydrous magnesium silicate. The filtrate is evaporated in vacuo to give 0.40 g of a glass, m.p. 98°-117° C.; Anal. Calc'd: C, 62.9; H, 4.7; N, 16.3; Cl, 11.6. Found: C, 62.4; H, 4.3; N, 15.6; Cl, 11.7.

Workup

  1. temperatureis heated at 70°-80° C. for 1 hour
  2. temperatureThe mixture is chilled
  3. extractionextracted (several times) with ethyl acetate
  4. customThe filtrate is evaporated
  5. dissolutionthe residue dissolved in dichloromethane
  6. customThe filtrate is evaporated in vacuo

Sources & evidence

ORD record
ord-7e0c6eadead34c72bf40da10875fa209
Source dataset
uspto-grants-1996_05
Patent number
US05516774

Reaction notes

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