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

HRID 341825Notes

Reaction equation

HRID 341825 reaction equation
C([O-])(=O)C.[K+].Cl[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][N:18]3[C:22]4=[N:23][C:24]([CH3:28])=[CH:25][C:26]([CH3:27])=[C:21]4[N:20]=[C:19]3[CH2:29][CH3:30])[CH:15]=2)[N:10]=[C:9]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[N+:37]([O-])=O)[CH:8]=1.C(O)C>[C].[Pd].C(OCC)(=O)C.O.C(Cl)(Cl)Cl>[CH2:29]([C:19]1[N:18]([CH2:17][C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[N:10]=[C:9]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[NH2:37])[CH:8]=[CH:7]3)[C:22]2=[N:23][C:24]([CH3:28])=[CH:25][C:26]([CH3:27])=[C:21]2[N:20]=1)[CH3:30]

Participants

8

Reactant 3

HCID 702EthanolHCID 517044Potassium AcetateHCID 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 76.1%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To 2.04 g of a 5% palladium-carbon catalyst, 15 ml of water containing 10.2 g of potassium acetate was added. Then, a solution of 10.18 g (21.6 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 dissolved in 30 ml of ethyl acetate and 240 ml of ethanol at 70° C. was added thereto, and the thus-prepared mixture was stirred under a hydrogen atmosphere at 60° C. for 3 hours. After adding 150 ml of chloroform and 200 ml of water thereto, the thus-prepared mixture was filtered through celite. The resulting filtrate was separated out, and the organic layer obtained was concentrated to 95.0 g in an evaporator. After allowing to stand at 0° C., the crystals precipitated were collected by filtration. The resulting filtration residue was washed with 10 ml of ethanol three times and dried under reduced pressure at 40° C. to obtain 6.70 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. customThe resulting filtrate was separated out
  3. customthe organic layer obtained
  4. concentrationwas concentrated to 95.0 g in an evaporator
  5. customto stand at 0° C.
  6. customthe crystals precipitated
  7. filtrationwere collected by filtration
  8. filtrationThe resulting filtration residue
  9. washwas washed with 10 ml of ethanol three times
  10. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-a86073e018b74c3087ffba3081931796
Source dataset
uspto-grants-1999_01
Patent number
US05856337

Reaction notes

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