Methanol → Pyrrolo(3,4-e)(1,4)diazepin-2(1H)-one, 3,7-dihydro-6-methyl-5-phenyl-

HRID 2397528Notes

Reaction equation

HRID 2397528 reaction equation
C([C:9]1[C:13]([NH:14][C:15](=[O:28])[CH2:16][N:17]2[C:21](=O)[C:20]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]3C2=O)=[CH:12][N:11](C)[CH:10]=1)(=O)C1C=CC=CC=1.NN.[CH3:32]O>>[CH3:32][C:10]1[NH:11][CH:12]=[C:13]2[C:9]=1[C:21]([C:20]1[CH:19]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[N:17][CH2:16][C:15](=[O:28])[NH:14]2

Participants

4

Reactant 3

HCID 887MethanolHCID 9321HydrazineHCID 54304491HCID 54304491, compound

Product 1

HCID 198359Pyrrolo(3,4-e)(1,4)diazepin-2(1H)-one, 3,7-dihydro-6-methyl-5-phenyl-

Procedure

3-Benzoyl-1-methyl-4-(phthalimidoacetamido)pyrrole (38 g.) is reacted with 6 g. of anhydrous hydrazine in 300 ml. of methanol according to the procedure of the foregoing example. After evaporation of the solvent and refluxing the residue with concentrated hydrochloric acid, the reaction mixture is filtered and the filtrate is alkalinized with dilute sodium hydroxide. The precipitate is crystallized from methanol. Yield 19 g. The compound decomposes at 400° C. without melting.

Workup

  1. customAfter evaporation of the solvent
  2. temperaturerefluxing the residue with concentrated hydrochloric acid
  3. filtrationthe reaction mixture is filtered
  4. customThe precipitate is crystallized from methanol
  5. customdecomposes at 400° C.

Sources & evidence

ORD record
ord-9954e9538a5e4150b7e2fb9238b091a9
Source dataset
uspto-grants-1977_05
Patent number
US04022766

Reaction notes

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