Nitric Acid → (S)-(+)-1,2,3,11a-tetrahydro-7-nitro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione

HRID 851644Notes

Reaction equation

HRID 851644 reaction equation
[CH2:1]1[C@H:5]2[C:6](=[O:16])[NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10](=[O:11])[N:4]2[CH2:3][CH2:2]1.[N+:17]([O-])([OH:19])=[O:18]>>[N+:17]([C:13]1[CH:14]=[CH:15][C:8]2[NH:7][C:6](=[O:16])[C@@H:5]3[CH2:1][CH2:2][CH2:3][N:4]3[C:10](=[O:11])[C:9]=2[CH:12]=1)([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 677114(S)-(+)-2,3-Dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione

Product 1

HCID 53877430(S)-(+)-1,2,3,11a-tetrahydro-7-nitro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione

Procedure

130 ml of 89 percent nitric acid are treated portionwise at room temperature over a period of 1.5 hours with 43.0 (199 mmol) of (S)-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione. The mixture is stirred at room temperature for 18 hours and poured into 1.5 l of ice-water. The precipitated material is filtered off under suction, washed with a large amount of water and dried at 80° in vacuo. There is obtained (S)-(+)-1,2,3,11a-tetrahydro-7-nitro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione of melting point 259°-261°.

Workup

  1. filtrationThe precipitated material is filtered off under suction
  2. washwashed with a large amount of water
  3. customdried at 80° in vacuo

Sources & evidence

ORD record
ord-474a1cf171654466a618dd96ee8fa5b9
Source dataset
uspto-grants-1983_05
Patent number
US04386028

Reaction notes

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