Lithium Hydroxide → 6-(2-methylpropoxy)pyridine-3-carboxylic acid

HRID 1099427Notes

Reaction equation

HRID 1099427 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[CH:4][N:3]=1.[OH-].[Li+].C(OC1C=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20]N=1)C>CC(C)CO>[CH2:22]([O:23][C:2]1[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1)[CH:21]([CH3:25])[CH3:20]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 2799611Ethyl 6-chloronicotinateHCID 64858176-Ethoxypyridine-3-carboxylic acid

Product 1

HCID 201208616-(2-methylpropoxy)pyridine-3-carboxylic acidYield 25%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Conditions

Temperature
35 °C

Procedure

The title compound was synthesized as described for Intermediate example I-81 in 25% yield starting from ethyl 6-chloronicotinate and 2-methylpropan-1-ol. The reduction was performed using 3 equiv of lithium hydroxide, the reaction mixture was stirred at 35° C. over night. The product contains 58% of 6-ethoxynicotinic acid; MS (ESI) m/z 194[M−H+].

Sources & evidence

ORD record
ord-06a93e42733d453585c5cb7252fc5f95
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

Loading…