Sodium hydride → HCID 19592839, compound

HRID 613585Notes

Reaction equation

HRID 613585 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:11]1[C:20]2[C:15](=[C:16]([NH:21][C:22](=[O:31])[C:23]3[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:30])[CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[CH3:32]>CN1CCCC1=O>[Cl:30][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([Cl:29])[C:23]=1[C:22]([NH:21][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[N:14]=[CH:13][C:12]([CH3:32])=[C:11]2[N:5]1[CH:6]=[CH:7][C:2](=[O:1])[CH:3]=[CH:4]1)=[O:31]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19592456HCID 19592456, compoundHCID 178418642HCID 178418642, compound

Product 1

HCID 19592839HCID 19592839, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 4-hydroxypyridine (114 mg) in N-methylpyrrolidone (3 ml) was added sodium hydride (60% in oil, 28.9 mg) under ice-cooling, and the mixture was stirred for 30 minutes. To the mixture was added 4-chloro-8-(2,6-dichlorobenzoylamino)-3-methylquinoline (200 mg), and the mixture was stirred for 1.5 hours at 120° C. The mixture was extracted with ethyl acetate, and the extract was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (ethyl acetate-methanol-dichloromethane) and crystallized from diethyl ether to give 8-(2,6-dichlorobenzoylamino)-3-methyl-4-(1,4-dihydro-4-oxopyridin-1-yl)quinoline (185 mg) as white crystal.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1.5 hours at 120° C
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (ethyl acetate-methanol-dichloromethane)
  8. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-a49f50dbffbd4e9b88dd098d95e2cd7f
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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