Sodium Hydroxide → HCID 11392136, compound

HRID 917789Notes

Reaction equation

HRID 917789 reaction equation
C([O:3][C:4]([C:6]1[C:11]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][C:14]=2[F:21])=[CH:10][C:9](=[O:22])[N:8]([CH3:23])[CH:7]=1)=[O:5])C.[OH-].[Na+]>CCO>[CH2:19]([C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:11]2[C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]([CH3:23])[C:9](=[O:22])[CH:10]=2)=[C:14]([F:21])[CH:15]=1)[CH3:20]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11427124HCID 11427124, compound

Product 1

HCID 11392136HCID 11392136, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

4-(4-Ethyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester (9.20 g, 28.90 mmol) was dissolved in EtOH (100 mL) and treated with NaOH (3.50 g, 86.70 mmol). This mixture was stirred at 90° C. for 2 hours to hydrolyze the ester as in Example 1, alternate Step C to give 4-(4-Ethyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid as a white solid (8.30 g, 98%). 1H NMR [(CD3)2SO, 400 MHz] δ 13.21 (v br s, 1H), 9.41 (s, 1H), 8.49 (s, 1H), 7.35 (dd, J=10.1, 1.9 Hz, 1H), 7.19 (dd, J=8.4, 1.7, 0.8 Hz, 1H), 7.06 (dd, J=8.5 1.9 Hz, 1H), 5.33 (dd, J=0.7 Hz, 1H), 3.37 (s, 3H), 2.57 (q, J=7.2 Hz, 2H). 1.16 (t, J=7.1 Hz, 3H). (APCI+) calcd for C15H15FN2O3 290.29 (M+1), found 291.1.

Sources & evidence

ORD record
ord-48dada77ea474974aeb15b19e0365fdb
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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