Sodium Hydroxide → 10-bromo-5-carboxy-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-one

HRID 850778Notes

Reaction equation

HRID 850778 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:19]=[C:18]([C:20]([O:22]CC)=[O:21])[C:17](=[O:25])[C:8]4[CH:9]=[C:10]([O:15][CH3:16])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4.[OH-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[C:17](=[O:25])[C:8]4[CH:9]=[C:10]([O:15][CH3:16])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2125285710-bromo-5-ethoxycarbonyl-2-methoxy-4H-pyrido [3,2,1-jk]carbazole-4-one

Product 1

HCID 2125282410-bromo-5-carboxy-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 83.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10-bromo-5-ethoxycarbonyl-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-one (400 mg) obtained in Example 98 was suspended in ethanol (10 ml), and 1N sodium hydroxide (3 ml) was added. The mixture was stirred at room temperature for 12 hours, and the solvent was evaporated under reduced pressure. To the residue was added 1N hydrochloric acid to pH 1, and the crystals precipitated were recovered by filtration, and washed with ethanol and ether to obtain the title compound (310 mg, 83%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionTo the residue was added 1N hydrochloric acid to pH 1
  3. customthe crystals precipitated
  4. filtrationwere recovered by filtration
  5. washwashed with ethanol and ether

Sources & evidence

ORD record
ord-eb1ca7c767a94670b4a82836f5b06137
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

Loading…