Sodium methanolate methanol → HCID 178493183, compound

HRID 2267095Notes

Reaction equation

HRID 2267095 reaction equation
Br[C:2]1[C:3]([CH3:20])=[N:4][CH:5]=[C:6]([C:18]=1[OH:19])[C:7]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[O:8].[CH3:21][O-:22].[Na+].CO>CN(C)C=O.[Cu]I>[F:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][NH:9][C:7](=[O:8])[C:6]2[C:18]([OH:19])=[C:2]([O:22][CH3:21])[C:3]([CH3:20])=[N:4][CH:5]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 23694274Sodium methanolate methanolHCID 178432814HCID 178432814, compound

Product 1

HCID 178493183HCID 178493183, compoundYield 870%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

The compound 21 (75.2 g, 222 mmol) and copper (I) iodide (21.1 g, 111 mmol) were dissolved in dimethylformamide (750 ml), a 28% sodium methoxide-methanol solution (216 ml, 888 mmol) was added, and the mixture was stirred at 105° C. for 100 minutes. After cooling, ice-water (800 ml) was added, and unnecessary matter were filtered. To the solution was added 2M hydrochloric acid (443 ml), and crystals were collected by filtration. N-(4-fluorobenzyl)-4-hydroxy-5-methoxy-6-methylnicotinamide 22 (56.0 g, 870%) was obtained as a colorless crystal.

Workup

  1. temperatureAfter cooling
  2. filtrationunnecessary matter were filtered
  3. additionTo the solution was added 2M hydrochloric acid (443 ml), and crystals
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-4e9e4e3c1be943dabdacf854da6780dd
Source dataset
uspto-grants-2010_12
Patent number
US07858788B2

Reaction notes

Loading…