Methanol → HCID 14075324, compound

HRID 2107903Notes

Reaction equation

HRID 2107903 reaction equation
[CH3:1][N:2]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10](=[O:19])[C:4]([C:5]([O:7]CC)=[O:6])=[C:3]1[CH2:20][CH2:21][CH3:22].CO.O>[OH-].[Na+]>[CH3:1][N:2]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10](=[O:19])[C:4]([C:5]([OH:7])=[O:6])=[C:3]1[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 22159846HCID 22159846, compound

Product 1

HCID 14075324HCID 14075324, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
85 °C

Procedure

4.5 g (0.015 mol) of ethyl 1-methyl-6-phenyl-2-propyl-4-oxonicotinate is suspended in 60 g of 5% sodium hydroxide in a 1:1 mixture of methanol and water. The mixture is heated at 85° C. and stirred for 21/2 hrs. The solution formed is acidified and the suspension formed is vacuum filtered. The filter cake is dried to afford 2.7 g of 1-methyl-6-phenyl-2-propyl-4-oxonicotinic acid, mp 150° C. (MDC/ether). An additional 0.5 g of 1-methyl-6-phenyl-2-propyl-4-oxonicotinic acid is obtained by extraction of the xylene solution with 30 ml of 1% sodium hydroxide and acidification of the basic extract.

Workup

  1. customThe solution formed
  2. customthe suspension formed
  3. filtrationfiltered
  4. customThe filter cake is dried

Sources & evidence

ORD record
ord-07d5158b3baa4484a4794fdbc491fcb9
Source dataset
uspto-grants-1990_06
Patent number
US04936904

Reaction notes

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