Hydrazine hydrate (1:1) → HCID 70296521, compound

HRID 1421214Notes

Reaction equation

HRID 1421214 reaction equation
[N+:1]([C:4]1[CH:27]=[CH:26][C:7]([CH:8]=[CH:9][C:10]2[C:16]3[CH:17]=[C:18]([O:23][CH3:24])[C:19]([O:21][CH3:22])=[CH:20][C:15]=3[CH2:14][CH:13]([CH3:25])[NH:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O.O.NN>CO.[Ni]>[NH2:1][C:4]1[CH:27]=[CH:26][C:7]([CH:8]=[CH:9][C:10]2[C:16]3[CH:17]=[C:18]([O:23][CH3:24])[C:19]([O:21][CH3:22])=[CH:20][C:15]=3[CH2:14][CH:13]([CH3:25])[NH:12][N:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 70296504HCID 70296504, compound

Product 1

HCID 70296521HCID 70296521, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

6.95 g (18.9 mmoles) of 1-(4-nitrostyryl)-4-methyl-7,8-dimethoxy-3,4-dihydro-5H-2,3-benzodiazepine prepared according to Example 25 are suspended in 170 ml of methanol, 0.7 g of dry (corresponding to about 1.4 g of wet) Raney nickel catalyst and 3.3 ml (66 mmoles) of 100% hydrazine hydrate are added to it and the reaction mixture is stirred for 1 hour. A solution is obtained, and in the beginning the inner temperature rises to 40-45° C. The catalyst is filtered off, washed three times with 15 ml each of methanol, the filtrate is evaporated in vacuo, the crude product is conveyed to a filter with 80 ml of water, washed three times with 15 ml each of water and dried. Thus 5.46 g of product are obtained. In order to purify the crude product it is recrystallized from 25 ml of 50% ethanol. Thus 4.21 g (66.0%) of the desired product are obtained. M.p.: 152-154° C.

Workup

  1. additionare added to it
  2. customA solution is obtained
  3. customrises to 40-45° C
  4. filtrationThe catalyst is filtered off
  5. washwashed three times with 15 ml each of methanol
  6. customthe filtrate is evaporated in vacuo
  7. filtrationa filter with 80 ml of water
  8. washwashed three times with 15 ml each of water
  9. customdried

Sources & evidence

ORD record
ord-1663262b0a074e12bbc5293f7ff2af95
Source dataset
uspto-grants-2000_06
Patent number
US06075018

Reaction notes

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