Methanol → 2-{6-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]quinolin-2-yl}aniline

HRID 341824Notes

Reaction equation

HRID 341824 reaction equation
CO.[OH-].[K+].Cl[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][N:17]3[C:21]4=[N:22][C:23]([CH3:27])=[CH:24][C:25]([CH3:26])=[C:20]4[N:19]=[C:18]3[CH2:28][CH3:29])[CH:14]=2)[N:9]=[C:8]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[N+:36]([O-])=O)[CH:7]=1>[C].[Pd].C(Cl)(Cl)Cl>[CH2:28]([C:18]1[N:17]([CH2:16][C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[N:9]=[C:8]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[NH2:36])[CH:7]=[CH:6]3)[C:21]2=[N:22][C:23]([CH3:27])=[CH:24][C:25]([CH3:26])=[C:20]2[N:19]=1)[CH3:29]

Participants

6

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 153844004-chloro-6-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]-2-(nitrophenyl)quinoline

Product 1

HCID 154636382-{6-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]quinolin-2-yl}anilineYield 47.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To 240 ml of methanol containing 8.0 g of potassium hydroxide, 8.12 g (17.2 mmol) of 4-chloro-6-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]-2-(nitrophenyl)quinoline obtained in Example 4 and 0.80 g of a 5% palladium-carbon catalyst were added and the thus-prepared mixture was stirred under a hydrogen atmosphere for 17 hours. After adding 120 ml of chloroform thereto, the thus-prepared mixture was filtered through celite. To the resulting filtrate, 120 ml of water was added, and the thus-prepared mixture was then separated out. The resulting organic layer was washed with 120 ml of water. Then, 60 ml of water was added to the organic layer, and a 130 ml portion thereof was distilled off by heating under atmospheric pressure. After allowing to stand at 0° C., the crystals precipitated were collected by filtration, and the resulting filtration residue was further recrystallized from a mixture of chloroform with methanol to obtain 3.30 g of 2-{6-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]quinolin-2-yl}aniline.

Workup

  1. filtrationthe thus-prepared mixture was filtered through celite
  2. additionTo the resulting filtrate, 120 ml of water was added
  3. customthe thus-prepared mixture was then separated out
  4. washThe resulting organic layer was washed with 120 ml of water
  5. additionThen, 60 ml of water was added to the organic layer
  6. distillationa 130 ml portion thereof was distilled off
  7. temperatureby heating under atmospheric pressure
  8. customto stand at 0° C.
  9. customthe crystals precipitated
  10. filtrationwere collected by filtration
  11. filtrationthe resulting filtration residue
  12. customwas further recrystallized from a mixture of chloroform with methanol

Sources & evidence

ORD record
ord-a8df409a34cb41c6999249f660e813e8
Source dataset
uspto-grants-1999_01
Patent number
US05856337

Reaction notes

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