Tetrahydrofuran → 6-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylic acid

HRID 1191692Notes

Reaction equation

HRID 1191692 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11](=[O:14])[N:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=1)=[O:7].O1CCCC1>O>[O:14]=[C:11]1[N:10]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:13]=[CH:12]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 11989075Methyl 6-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 119888126-Oxo-1-phenyl-1,6-dihydropyridine-3-carboxylic acidYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Lithium hydroxide monohydrate (0.366 g, 8.73 mmol) was added to a mixture of methyl-6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate (1.0 g, 4.37 mmol), tetrahydrofuran (9 mL) and water (6 mL) at 0° C. The mixture was stirred for 1 hour, diluted with water and washed with ethyl acetate. The pH of the aqueous layer was adjusted to 2 using 2 N hydrochloric acid and the precipitate was filtered to give the title compound as a brown solid (0.740 g, 79%). m.p. 256-263° C.; 1H NMR (400 MHz, DMSO-d6) δ 6.53 (d, J=9.4 Hz, 1H), 7.40-7.49 (m, 5H), 7.87 (dd, J=2.5, 9.8 Hz, 1H), 8.23 (d, J=2.5 Hz, 1H); IR (KBr) υ 3446, 1708, 1645, 1577, 1263, 1228 cm−1; MS 214 (M−1).

Workup

  1. washwashed with ethyl acetate
  2. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-2c7b42847cab449a84ffa31e54c21e6f
Source dataset
uspto-grants-2014_03
Patent number
US08680123B1

Reaction notes

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