Ethylene Glycol → 2-Amino-5-(4-chlorophenyl)pyridine-3-carboxylic acid

HRID 1980306Notes

Reaction equation

HRID 1980306 reaction equation
[NH2:1][C:2]1C(C#N)=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:4][N:3]=1.[OH-:17].[K+].[CH2:19]([OH:22])[CH2:20]O>>[NH2:1][C:2]1[C:20]([C:19]([OH:22])=[O:17])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium HydroxideHCID 132426422-Amino-5-(4-chlorophenyl)pyridine-3-carbonitrile

Product 1

HCID 132426432-Amino-5-(4-chlorophenyl)pyridine-3-carboxylic acid

Procedure

An alkaline hydrolysis procedure may also be used to synthesize the desired compound. Accordingly, 2-amino-5-(4-chlorophenyl)-3-pyridinecarbonitrile (2.0 grams) and KOH (2.0 grams) in 30 ml ethylene glycol were heated at 150° C. in an oil bath. After 3 hours the reaction was complete and the alkaline solution was poured into ice water and acidified to give the desired solid. The final product was again confirmed by NMR, yield 2.3 grams, m.p. 300°-315° C. dec.

Workup

  1. customto give the desired solid

Sources & evidence

ORD record
ord-d58b553aad6e4b43a1ae06c17debfb69
Source dataset
uspto-grants-1985_04
Patent number
US04508722

Reaction notes

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