Sodium hydride → Nicotinic Acid

HRID 3926

Reaction equation

HRID 3926 reaction equation
S[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[Na].[H-].[Na+].C1[CH2:15][O:14]CC1.CN(C=[O:20])C>C1COCC1.O>[N:5]1[CH:6]=[CH:7][CH:2]=[C:3]([C:15]([OH:14])=[O:20])[CH:4]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 5360545SodiumHCID 21974620tetrahydrofuran N,N-dimethylformamideHCID 178418431pyridine-4-thiol2×

Product 1

HCID 938Nicotinic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5.2 g of 90% pyridinium bromide perbromide was added in one portion to a solution of 5 g of 3-pyridinecarboxylic acid, 5-cyano-1,4-dihydro-2,6-dimethyl-4-[2-(trifluoromethyl)phenyl]-, ethyl ester and 1.2 ml pyridine in 150 ml of dry ethanol-free CHCl3 at -10° C. The mixture was stirred for 45 minutes at 0° C. and the bromide (6 g) was obtained by flash chromatography over silica gel (10% EtAc/CH2Cl2). This was dissolved in 30 ml of THF and added dropwise to a suspension of 4-mercaptopyridine, sodium salt [(prepared from 1.5 g of 4-mercapto pyridine and 0.5 g of 60% NaH in THF/DMF (1:1, 40 ml)] at 0° C. and the mixture was warmed to room temperature. After stirring for one hour, the reaction mixture was diluted with water and extracted with CH2Cl2. The organic extracts were washed with water, dried, and evaporated. The residue was crystallized from EtAc to give 5.1 g of 3-pyridinecarboxylic acid, 5-cyano-1,4-dihydro-6-methyl-2[4-pyridinylthiomethyl]-4-[(2-trifluoromethyl)phenyl]-, ethyl ester, mp 222°-224° C.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic extracts were washed with water
  3. customdried
  4. customevaporated
  5. customThe residue was crystallized from EtAc

Sources & evidence

ORD record
ord-d3c2e62310254be1a1f64db4e6e7ec04
Source dataset
uspto-grants-1988_02
Patent number
US04723014

Linked notes

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