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

HRID 1099454Notes

Reaction equation

HRID 1099454 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+].[CH3:15][O:16][CH2:17][CH2:18][OH:19]>>[CH3:15][O:16][CH2:17][CH2:18][O:19][C:2]1[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 80192-MethoxyethanolHCID 2799611Ethyl 6-chloronicotinate

Product 1

HCID 150670936-(2-Methoxyethoxy)pyridine-3-carboxylic acidYield 67%

Conditions

Temperature
40 °C

Procedure

The title compound was synthesized as described for Intermediate example I-81 in 67% yield starting from ethyl 6-chloronicotinate and 2-methoxyethanol. The reduction was performed using 3 equiv of lithium hydroxide while heating to 40° C. over weekend. The final aqueous solution was extracted with ethyl acetate in order to collect the product; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.70 (d, 1 H), 8.13 (dd, 1 H), 6.91 (d, 1 H), 4.42-4.47 (m, 2 H), 3.62-3.68 (m, 2 H), 3.29 (s, 3 H); MS (ESI) m/z 198[M+H+].

Workup

  1. extractionThe final aqueous solution was extracted with ethyl acetate in order
  2. customto collect the product

Sources & evidence

ORD record
ord-65c7e6c0032e4ba096dfc25c01b720ff
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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