2-Pyridinecarboxaldehyde → 10-bromo-2-methoxy-5-(2-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-one

HRID 850773Notes

Reaction equation

HRID 850773 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH2:19][CH2:18][C:17](=[O:20])[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.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]=O.[OH-].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:19]=[C:18]([CH2:27][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=4)[C:17](=[O:20])[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

6

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 988395610-bromo-5,6-dihydro-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-one

Product 1

HCID 1936490010-bromo-2-methoxy-5-(2-pyridylmethyl)-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 63%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

10-bromo-5,6-dihydro-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-one (0.7 g) obtained in Example 1, step 3 was suspended in ethanol (30 ml), and pyridine-2-aldehyde (0.7 g) and sodium hydroxide (0.3 g) dissolved in water (5 ml) were added at room temperature. The mixture was stirred at room temperature for 12 hours, and approximately half of the solvent was evaporated under reduced pressure. The precipitated crystals were recovered by filtration, and washed with water, ethanol and ether in succession to obtain the title compound (0.56 g, 61%).

Workup

  1. additionwere added at room temperature
  2. customapproximately half of the solvent was evaporated under reduced pressure
  3. filtrationThe precipitated crystals were recovered by filtration
  4. washwashed with water, ethanol and ether in succession

Sources & evidence

ORD record
ord-a2d1ce99ceaf4efd9bcc68bc1aa2aa7d
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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