Hydrochloric Acid → 5-hydroxy-2-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one hydrochloride

HRID 1519030Notes

Reaction equation

C([O:8][C:9]1[C:10](=[O:21])[CH:11]=[C:12]([CH3:20])[N:13]([CH2:15][C:16]([F:19])([F:18])[F:17])[CH:14]=1)C1C=CC=CC=1.[ClH:22]>C(O)(C)C>[ClH:22].[OH:8][C:9]1[C:10](=[O:21])[CH:11]=[C:12]([CH3:20])[N:13]([CH2:15][C:16]([F:17])([F:18])[F:19])[CH:14]=1

Participants

Conditions

Temperature: 110 °C

Procedure

5-(Benzyloxy)-2-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one (45.8 g, 164 mmol) was mixed with 6N HCl (100 mL) and isopropanol (20 mL). The mixture was heated at 110° C. oil bath for 8 hours and then concentrated by rotary evaporator. The residue was triturated with acetone and ether to give 5-hydroxy-2-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one hydrochloride (24.5 g). Yield=65%; 1H NMR (MeOD-D4, 90 MHz) δ (ppm): 8.18 (s, 1H), 7.21 (s, 1H), 5.31 (q, J=8.2 Hz, 2H) and 2.67 (s, 3H).

Workup

concentrationconcentrated by rotary evaporator
customThe residue was triturated with acetone and ether

Sources & evidence

ORD record: ord-4c3c0be1d44c453789ac5aa3c463c9cc
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073865B2

Reaction notes

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