Sodium Bicarbonate → HCID 19364875, compound

HRID 1531010Notes

Reaction equation

HRID 1531010 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]3[CH:19]=[C:18]([CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:17](=[O:27])[C:10]4[CH:11]=[CH:12][CH:13]=[C:14]([C:15]=2[CH:16]=1)[C:9]3=4)(=[O:3])[CH3:2].B.[Na].C(=O)([O-])O.[Na+]>CO.[OH-].[Na+]>[CH2:20]([C:18]1[C:17](=[O:27])[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]3[C:9]=2[N:8]([CH:19]=1)[C:7]1[CH:6]=[CH:5][C:4]([CH:1]([OH:3])[CH3:2])=[CH:16][C:15]3=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 21252848HCID 21252848, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 19364875HCID 19364875, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 887MethanolSolvent

Procedure

10-acetyl-5-benzyl-4H-pyrido[3,2,1-jk]carbazole-4-one (150 mg) produced in Example 196 was suspended in methanol (15 ml), and 1N sodium hydroxide (1 drop) was added. The mixture was cooled in an ice bath, and sodium boron hydride (161 mg) was gradually added. After stirring the mixture at room temperature for 1 hour, a small amount of saturated sodium hydrogencarbonate was added to the reaction mixture, and the solution was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residual crude crystals were washed with a mixed solvent of ether and hexane to obtain the title compound (126 mg, 83%).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. washThe residual crude crystals were washed with a mixed solvent of ether and hexane

Sources & evidence

ORD record
ord-0a20e7a0da834ac8842717c04f0f797c
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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