Ethanol → 10-bromo-2-carboxymethyloxy-5-methyl-4H-pyrido[3,2,1-jk]carbazole-4-one

HRID 850758Notes

Reaction equation

HRID 850758 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:24]=[C:23]([CH3:25])[C:22](=[O:26])[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>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:24]=[C:23]([CH3:25])[C:22](=[O:26])[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

4

Reactant 2

HCID 702EthanolHCID 1936490610-bromo-2-ethoxycarbonylmethyloxy-5-methyl-4H-pyrido[3,2,1-jk]carbazole-4-one

Product 1

HCID 1936493110-bromo-2-carboxymethyloxy-5-methyl-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10-bromo-2-ethoxycarbonylmethyloxy-5-methyl-4H-pyrido[3,2,1-jk]carbazole-4-one (200 mg) obtained in Example 52 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 90 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 (170 mg, 91%).

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-0a563d6c799b42168910c315e72da56b
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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