Nitric Acid → 9-bromo-2-(3-hydroxypropyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one nitrate

HRID 850813Notes

Reaction equation

HRID 850813 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:20](=[O:30])[C:21]([CH2:23][C:24]5[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=5)=[CH:22][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:10]=3.[N+:31]([O-:34])([OH:33])=[O:32]>CO>[N+:31]([O-:34])([OH:33])=[O:32].[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:20](=[O:30])[C:21]([CH2:23][C:24]5[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=5)=[CH:22][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15][CH2:16][CH2:17][CH2:18][OH:19])[CH:10]=3

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 98724899-bromo-2-(3-hydroxypropyloxy)-5-(3-pyridylmethyl)-4H-pyrido [3,2,1-jk]carbazole-4-one

Product 1

HCID 193649049-bromo-2-(3-hydroxypropyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one nitrateYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

9-bromo-2-(3-hydroxypropyloxy)-5-(3-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one (50 mg) obtained in Example 110 was suspended in methanol (100 ml) and to the suspension was added a solution of nitric acid (11 mg) in methanol (5 ml) at room temperature. The mixture was stirred for 30 minutes. The solvent was evaporated under reduced pressure, and the resulting crude crystals were washed with a small amount of methanol and ether in succession to obtain the title compound (47 mg, 83%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washthe resulting crude crystals were washed with a small amount of methanol and ether in succession

Sources & evidence

ORD record
ord-0f811f97a36840e18462d2be49a1af17
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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