Methanol → HCID 178493650, compound

HRID 2289951Notes

Reaction equation

HRID 2289951 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([F:23])=[C:17]([F:24])[C:16]=3F)=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28][OH:29].O>CN(C=O)C.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[CH:13]=[N:14][C:15]3[C:20]([C:21]=2[OH:22])=[CH:19][C:18]([F:23])=[C:17]([F:24])[C:16]=3[O:29][CH3:28])=[O:11])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24758Sodium hydride2×HCID 178522923HCID 178522923, compound

Product 1

HCID 178493650HCID 178493650, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

N-((4-Chlorophenyl)methyl)-4-hydroxy-6,7,8-trifluoro-3-quinolinecarboxamide (366 mg) from Example No. 15 and sodium hydride (60% dispersion, 40 mg) are dissolved in DMF (10 mL) and to the mixture is added methanol (200 μL). Additional sodium hydride (40 mg) is added, and the mixture is heated at 140° C. for 1 h. The reaction mixture is allowed to cool to rt, poured into water (50 mL), acidified with acetic acid (10 mL), and is filtered. The crude product is purified by column chromatography (hexane/2-propanol, 95/5) to afford 68 mg of the title compound as a white solid.

Workup

  1. temperatureto cool to rt
  2. filtrationis filtered
  3. customThe crude product is purified by column chromatography (hexane/2-propanol, 95/5)

Sources & evidence

ORD record
ord-cea067265dcd492489737bffe25f5e11
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

Loading…