Dimethylformamide → HCID 70417046, compound

HRID 649271Notes

Reaction equation

HRID 649271 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[C:6]([CH2:13][OH:14])=[C:5]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1F.CN(C)C=[O:25]>O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]3[CH:6]([CH2:7][N:8]=[C:20]4[C:15]=3[CH:16]=[CH:17][CH:18]=[CH:19]4)[C:13](=[O:14])[O:25][C:9]2=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 12245445HCID 12245445, compound

Product 1

HCID 70417046HCID 70417046, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride suspension (50% in mineral oil), 10 g, was washed with hexane and added to a solution of 20 g (0.066 mol) of the 6-chloro-4-(2-fluorophenyl)-3-hydroxymethylquinolin-2(1H)one in 350 ml of dimethylformamide. This mixture was stirred and refluxed under an atmosphere of nitrogen for 5 min. The cool reaction mixture was diluted with water and the product was precipitated by acidifying with 1N hydrochloric acid. It was collected, washed with water and recrystallized from dimethylformamide to yield final product with mp>350°.

Workup

  1. washSodium hydride suspension (50% in mineral oil), 10 g, was washed with hexane
  2. temperaturerefluxed under an atmosphere of nitrogen for 5 min
  3. customThe cool reaction mixture
  4. customthe product was precipitated
  5. customIt was collected
  6. washwashed with water
  7. customrecrystallized from dimethylformamide

Sources & evidence

ORD record
ord-e313da122d70425c85874ba084af21e7
Source dataset
uspto-grants-1988_04
Patent number
US04739049

Reaction notes

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