Sodium hydride → 6-(3-Methylbutoxy)nicotinic acid

Reaction equation

Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.[H-].[Na+].[CH3:13][CH:14]([CH3:18])[CH2:15][CH2:16][OH:17]>>[CH3:13][CH:14]([CH3:18])[CH2:15][CH2:16][O:17][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 31260Isoamyl Alcohol

HCID 792226-Chloronicotinic acid

Product 1

HCID 222199276-(3-Methylbutoxy)nicotinic acid

Procedure

6-(3-Methylbutoxy)nicotinic acid was prepared from 6-chloronicotinic acid (0.50 g), 3-methyl-1-butanol (0.36 ml) and sodium hydride (60%, 0.32 g) according to the method described in Example 54 to give the product as a white solid (0.25 g, 38%): δH (400 MHz, DMSO-d6) 12.97 (1H, m), 8.71 (1H, d, J 2.5 Hz), 8.12 (1H, dd, J 8.5, 2.5 Hz), 6.87 (1H, d, J 8.5 Hz), 4.36 (2H, t, J 7 Hz), 1.75 (1H, nonet, J 6.5 Hz), 1.62 (2H, q, J 6.5 Hz) and 0.93 (6H, d, J 6.5 Hz); HPLC (XTERRA, 20/50, 220 nm) 99% (3.90 min).