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

HRID 1995602Notes

Reaction equation

HRID 1995602 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-f424521837f7436a8531715fd0b9e6ac
Source dataset
uspto-grants-1983_09
Patent number
US04405552

Reaction notes

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