Methanol → HCID 178493638, compound

HRID 2289952Notes

Reaction equation

HRID 2289952 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)[C:16]=3F)=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28][OH:29].O.CN([CH:34]=[O:35])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]([O:29][CH3:28])[C:16]=3[O:35][CH3:34])=[O:11])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 178522923HCID 178522923, compound

Product 1

HCID 178493638HCID 178493638, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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, 160 mg) are dissolved in DMF (10 mL) and to the mixture is added methanol (200 μL). The mixture is heated at 140° C. for 1 h. The reaction mixture is allowed to cool to rt, poured into water (40 mL), acidified with acetic acid (10 mL), and is filtered. The crude product is recrystalized from acetic acid/water and then from toluene to afford 174 mg of the title compound as a white solid.

Workup

  1. temperatureto cool to rt
  2. filtrationis filtered
  3. customThe crude product is recrystalized from acetic acid/water

Sources & evidence

ORD record
ord-1ed5725eee9d44bb9ee5463b6fce31c6
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

Loading…