Hydrazine → Pyrrolo(3,4-e)(1,4)diazepin-2(1H)-one, 3,7-dihydro-5,8-diphenyl-6-methyl-

HRID 2397527Notes

Reaction equation

HRID 2397527 reaction equation
NN.C([C:11]1[C:15]([NH:16][C:17](=[O:30])[CH2:18][N:19]2C(=O)[C:22]3=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]3[C:20]2=O)=[C:14](C2C=CC=CC=2)[NH:13][C:12]=1[CH3:37])(=O)C1C=CC=CC=1>>[C:21]1([C:20]2[C:11]3[C:15](=[C:14]([C:21]4[CH:22]=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:13][C:12]=3[CH3:37])[NH:16][C:17](=[O:30])[CH2:18][N:19]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:22]=1

Participants

3

Reactant 2

HCID 9321HydrazineHCID 12282573HCID 12282573, compound

Product 1

HCID 3044501Pyrrolo(3,4-e)(1,4)diazepin-2(1H)-one, 3,7-dihydro-5,8-diphenyl-6-methyl-

Procedure

To a solution of 7 g. of anhydrous hydrazine in 350 ml. of methano 27.8 g. of 3-benzoyl-2-methyl-5-phenyl-4-(phthalimidoacetamido)pyrrole are added and the mixture is refluxed for one hour. The solvent is evaporated off and 150 ml. of concentrated hydrochloric acid are added to the residue. After refluxing for one hour the solid precipitated is eliminated by filtration and the filtrate is diluted with water and then alkalinized with 10% sodium hydroxide. The precipitate is crystallized twice from methanol yielding 9 g. of the title product which melts at 310°-12° C.

Workup

  1. temperaturethe mixture is refluxed for one hour
  2. customThe solvent is evaporated off
  3. additionof concentrated hydrochloric acid are added to the residue
  4. temperatureAfter refluxing for one hour the solid
  5. customprecipitated
  6. filtrationis eliminated by filtration
  7. additionthe filtrate is diluted with water
  8. customThe precipitate is crystallized twice from methanol yielding 9 g

Sources & evidence

ORD record
ord-de2dc72c45214ed28f82e717993fa7b3
Source dataset
uspto-grants-1977_05
Patent number
US04022766

Reaction notes

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