Ethanol → 5-[(4-Fluorophenyl)methyl]-3-{[4-(methyloxy)phenyl]amino}-2-pyridinecarboxylic acid
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)C(C#N)=[N:13][CH:14]=2)=[CH:4][CH:3]=1.[OH-:26].[Na+].[CH2:28]([OH:30])[CH3:29]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:10]=[C:11]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C:29]([C:28]([OH:26])=[O:30])=[N:13][CH:14]=2)=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 100 °C
Procedure
5-[(4-fluorophenyl)methyl]-3-{[4-(methyloxy)phenyl]amino}-2-pyridinecarbonitrile (505 mg, 1.52 mmol) was dissolved in ethanol (50 mL) and 50% sodium hydroxide was added and the mixture was heated at 100° C. for 1 hour. The reaction was cooled to ambient temperature, concentrated under reduced pressure, and acidified with 6 N hydrochloric acid. The aqueous layer was extracted with ethyl acetate and the organics were dried over sodium sulfate and concentrated under reduced pressure to yield 5-[(4-fluorophenyl)methyl]-3-{[4-(methyloxy)phenyl]amino}-2-pyridinecarboxylic acid (560 mg, 95% yield). 1H NMR (CDCl3/methanol-d4) δ 7.95 (s, 1 H), 7.32 (s, 1 H), 7.01-6.98 (m, 4 H), 6.93-6.83 (m, 4 H), 3.86 (s, 2 H), 3.75 (s, 3 H); MS m/z 353 (M+1).
Workup
- temperatureThe reaction was cooled to ambient temperature
- concentrationconcentrated under reduced pressure
- extractionThe aqueous layer was extracted with ethyl acetate
- dry with materialthe organics were dried over sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d47f54e5f4d846b3aa8261907b6e1c85
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691991B2
Reaction notes
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