4-hydroxy-3-methyl-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-6,11-dione → HCID 20301691, compound

HRID 1732826Notes

Reaction equation

HRID 1732826 reaction equation
[OH:1][C:2]1[C:12]2[NH:11][C:10](=[O:13])[CH:9]3[CH2:14][CH2:15][CH2:16][N:8]3[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH3:18]>COC(OC)C1C=CC=CC=1>[CH3:18][C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:17])[N:8]3[CH2:16][CH2:15][CH2:14][CH:9]3[C:10](=[O:13])[N:11]3[CH:18]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:12][CH:2]=4)[O:1][C:2]=1[C:12]=23

Participants

3

Reactant 1

HCID 3239324-hydroxy-3-methyl-6a,7,8,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-6,11-dione

Product 1

HCID 20301691HCID 20301691, compoundYield 176.8%

Reagents, catalysts & solvents 1

HCID 62375Benzaldehyde dimethyl acetalSolvent

Procedure

2.0 g of 2,3,5,10,11,11a-hexahydro-9-hydroxy-8-methyl-1H-pyrrolo(2,1-C)(1,4)benzodiazepin-5,11-dione was admixed with 300 ml of benzaldehyde dimethyl acetal and heated at 190° to 200° C. for 2 hours with stirring under a stream of nitrogen gas. The liquid reaction mixture was concentrated at 130° to 150° C. under reduced pressure. The concentrate was dissolved in a small quantity of chloroform, passed through a silica gel chromatographic column and eluted with ether. Thus, there was obtained 2.4 g of 6,8,9,10,10a,11-hexahydro-3-methyl-1-phenyl-1H-oxazolo(5,4,3-jk)pyrrolo(2,1-C)(1,4)benzodiazepin-6,11-dione as a colorless crystal. Recrystallization of the resulting product from ether gave a colorless needle-like crystal having a melting point of 158.5° to 162.5° C.

Workup

  1. temperatureheated at 190° to 200° C. for 2 hours
  2. customThe liquid reaction mixture
  3. concentrationwas concentrated at 130° to 150° C. under reduced pressure
  4. dissolutionThe concentrate was dissolved in a small quantity of chloroform
  5. washeluted with ether

Sources & evidence

ORD record
ord-db3ea00a582e4538a81932888e709001
Source dataset
uspto-grants-1980_12
Patent number
US04239683

Reaction notes

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