Ethanol → 10-bromo-2-carboxymethyloxy-4H-pyrido[3,2,1-jk]carbazole-4-one

HRID 850768Notes

Reaction equation

HRID 850768 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:24]=[CH:23][C:22](=[O:25])[C:8]4[CH:9]=[C:10]([O:15][CH2:16][C:17]([O:19]CC)=[O:18])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4.C(O)C.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:24]=[CH:23][C:22](=[O:25])[C:8]4[CH:9]=[C:10]([O:15][CH2:16][C:17]([OH:19])=[O:18])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 2125284410-bromo-2-ethoxycarbonylmethyloxy-4H-pyrido [3,2,1-jk]carbazole-4-one

Product 1

HCID 1936485710-bromo-2-carboxymethyloxy-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10-bromo-2-ethoxycarbonylmethyloxy-4H-pyrido[3,2,1-jk]carbazole-4-one (200 mg) obtained in Example 62 was suspended in a mixed solution of ethanol (10 ml) and methylene chloride (10 ml), and 1N aqueous solution of sodium hydroxide (1 ml) was added to the suspension. The mixture was stirred at room temperature for 10 minutes, and the solvent was evaporated under reduced pressure. To the residue was added water and 1N hydrochloric acid to pH 1, and the crystals precipitated were recovered by filtration to obtain the title compound (160 mg, 84%).

Workup

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

Sources & evidence

ORD record
ord-a4c451ea807246a58643cdcbc665fce9
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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