Sodium Hydroxide → 4-(2-Fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

HRID 917695Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

4-(2-Fluoro-4-iodo-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester was dissolved in EtOH (100 mL) and treated with NaOH (2.60 g, 72.0 mmol). This mixture was stirred at 70° C. for 20 hours. The mixture was cooled to room temperature and solvent was removed under reduced pressure. The residue was acidified with 1N HCl then the resulting precipitate was filtered and washed with water. The solid was dried under high vacuum pump to afford 4-(2-Fluoro-4-iodo-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid as a white solid (9.0 g, 96%). 1H NMR [(CD3)2SO, 400 MHz] δ 13.27(v br s, 1H), 9.60 (s, 1H), 8.49 (s, 1H), 7.74 (dd, J=10.1, 1.9 Hz, 1H), 7.59 (dd, J=8.4, 1.7, 0.8 Hz, 1H), 7.29 (dd, J=8.5 Hz, 1H), 5.48 (dd, J=0.7 Hz, 1H), 3.38 (s, 3H). (APCI+) calcd for C13H10FIN2O3 388.13 (M−1), found 386.9.

Workup

temperatureThe mixture was cooled to room temperature
customsolvent was removed under reduced pressure
filtrationthe resulting precipitate was filtered
washwashed with water
customThe solid was dried under high vacuum pump

Sources & evidence

ORD record: ord-e52361a7af4d4b45b64b82ad3edf6d8b
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273877B2

Reaction notes

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