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Benzaldehyde → HCID 21252825, compound

HRID 1531001
Notes
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Reaction equation

HRID 1531001 reaction equation
[CH:1]1[CH:13]=[CH:12][C:11]2[C:14](=[O:17])[CH2:15][CH2:16][N:9]3[C:10]=2[C:2]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=13.C([Li])CCC.[CH:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Cl-].[NH4+]>O1CCCC1>[C:23]([C:15]1[C:14](=[O:17])[C:11]2[CH:12]=[CH:13][CH:1]=[C:2]3[C:10]=2[N:9]([CH:16]=1)[C:8]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]3=1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 25517Ammonium ChlorideHCID 2872345,6-Dihydro-4h-pyrido[3,2,1-jk]carbazol-4-oneHCID 178418339Butyllithium

Product 1

HCID 21252825HCID 21252825, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

5,6-dihydro-4H-pyrido[3,2,1-jk]carbazole-4-one (4 g) prepared by the procedure described in J.O.C., 24, 324 (1959) was dissolved in anhydrous tetrahydrofuran (160 ml). n-butyl lithium (solution in hexane, 15 ml) was added dropwise to the solution cooled in an acetone-dry ice bath, and the mixture was stirred for 30 minutes. Benzaldehyde (2 ml) dissolved in anhydrous tetrahydrofuran (80 ml) was gradually added dropwise to the solution cooled in an acetone-dry ice bath, and the mixture was stirred for 90 minutes. Saturated aqueous solution of ammonium chloride of an adequate amount was added to the reaction mixture, and the mixture was heated to room temperature, and 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 residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=5:1) to obtain the title compound (852 mg, 14%).

Workup

  1. temperaturecooled in an acetone-dry ice bath
  2. additionwas gradually added dropwise to the solution
  3. temperaturecooled in an acetone-dry ice bath
  4. stirringthe mixture was stirred for 90 minutes
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-acb7b81df8b245f58f3c892f923adc1e
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06197768B1

Reaction notes

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