Lithium hydroxide, monohydrate → [4-(5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-phenoxy]-acetic acid

HRID 11324Notes

Reaction equation

HRID 11324 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([C:19]#[N:20])[C:16](=[O:21])[NH:15][C:14]=2[CH3:22])=[CH:9][CH:8]=1)C.O.[OH-].[Li+]>O1CCOCC1.O>[C:19]([C:17]1[C:16](=[O:21])[NH:15][C:14]([CH3:22])=[C:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:23])=[O:3])=[CH:8][CH:9]=2)[CH:18]=1)#[N:20]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15682655[4-(5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)phenoxy]-acetic acid ethyl ester

Product 1

HCID 11514722[4-(5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-phenoxy]-acetic acidYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of [4-(5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)phenoxy]-acetic acid ethyl ester (7, 1.3 g, 4.16 mmol) in a mixture of 1,4-dioxane (25 mL) and water (25 mL) was added lithium hydroxide mono hydrate (700 mg, 16.7 mmol). The reaction mixture was stirred for 2 h at ambient temperature, diluted with water (50 mL), washed with diethylether (2×25 mL), cooled to 0° C. and acidified to pH 2 with aqueous hydrochloric acid (5 N). After standing at ambient temperature overnight the formed precipitate was filtered off with suction, washed with water and dried under vacuum to give [4-(5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-phenoxy]-acetic acid (8) as light yellow crystalline solid (758 mg, 64% yield, 97% pure by LC-MS and 1H NMR), 1H NMR (400 MHz; CDCl3): δ 7.70 (d, 1H); 7.20 (m, 2H); 6.73 (m, 2H); 4.88 (s, 2H); 1.71 (s, 3H).

Workup

  1. washwashed with diethylether (2×25 mL)
  2. temperaturecooled to 0° C.
  3. waitAfter standing at ambient temperature overnight
  4. filtrationthe formed precipitate was filtered off with suction
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-22332d90ab204b59b4587a38c7a50d0f
Source dataset
uspto-grants-2006_08
Patent number
US07098211B2

Reaction notes

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