Acetic Acid → 4-Chloro-3,5-difluoro-2-(1-hydroxy-2-propyl)pyridine

HRID 1873Notes

Reaction equation

[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([CH:9]([CH3:18])[CH2:10][O:11]C2CCCCO2)[C:3]=1[F:19].O.C(O)(=O)C>C1COCC1>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([CH:9]([CH3:18])[CH2:10][OH:11])[C:3]=1[F:19]

Participants

Conditions

Temperature: 45 °C

Procedure

The product of Step 1 is dissolved in 200 mL of 2:1 THF:water and to this solution is added 6 mL of acetic acid. The reaction mixture is heated at 45° C. for approximately 5 hours. The THF is removed under reduced pressure and the aqueous reaction mixture is adjusted to a pH in the range of 8 to 9 with 10% sodium carbonate and is then extracted with methylene chloride. The organic layer is dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford the title compound.

Workup

customThe THF is removed under reduced pressure
extractionis then extracted with methylene chloride
dry with materialThe organic layer is dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4f295b3d715849a297bcad06075e2348
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05726182

Reaction notes

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