Ammonia → HCID 178418479, compound

HRID 1073310Notes

Reaction equation

[CH:1]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6]O[C:3](=[O:4])[CH:2]=1.[NH3:11]>>[OH:4][C:3]1[CH:2]=[CH:1][C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:11]=1

Participants

Reactant 2

HCID 222Ammonia

HCID 68141Coumalic acid

Product 1

HCID 178418479HCID 178418479, compound

Procedure

2-Hydroxypyridine or quinoline carboxylic acids and esters are useful as herbicide and pharmaceutical intermediates. One method for their preparation involves oxidizing quinolinic acid to obtain 2 3-bis(methoxycarbonyl)pyridine N-oxide, treating the N-oxide with acetic anhydride to give the 2-acetoxy compound, and hydrolyzing to give 6-hydroxy-2,3-dimethoxycarboxylpyridine in 27.5% overall yield; see E. Spinner et al., J. Chem. Soc. (B), 289 (1971). Another method involves reacting an ester of coumalic acid with ammonia to yield 2-hydroxy-5-pyridinecarboxylic acid; see W. T. Caldwell et al. J. Am. Chem. Soc. 66, 1479 (1944). Another method involves converting alpha-pyrone-6-carboxylic acid with ammonium acetate and glacial acetic acid into 2-pyridine-6-carboxylic acid; see J. Fried et al., J. Org. Chem. 6, 566 (1941).

Sources & evidence

ORD record: ord-776136bbcb8443b7b0c2b7e08aa6cb65
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04968803

Reaction notes

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