Hydrogen Bromide → 3-hydroxy-5-(2-methylphenethyl)pyridin-2(1H)-one

HRID 709080Notes

Reaction equation

C[O:2][C:3]1[C:8]([O:9]C)=[CH:7][C:6]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[CH:5][N:4]=1.Br.O>CO.[Pd].C(O)(=O)C>[OH:9][C:8]1[C:3](=[O:2])[NH:4][CH:5]=[C:6]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH:7]=1

Participants

Conditions

Temperature: 180 °C

Procedure

2,3-Dimethoxy-5-[(2-methylphenyl)ethynyl]pyridine (Intermediate 33) (437 mg, 1.7 mmol) was hydrogenated in methanol using palladium on carbon as catalyst at 20 bar. The crude product was dissolved in acetic acid (5 ml) and 48% aqueous hydrobromic acid (5 ml) was added before the mixture was irradiated in the microwave with heating at 180° C. for 1 hour. The resulting mixture was then poured into water and the precipitated solid was filtered off and washed with water before being recrystallised from ethanol (twice) to afford 3-hydroxy-5-(2-methylphenethyl)pyridin-2(1H)-one (70 mg, 0.3 mmol, 18% yield).

Workup

customwas irradiated in the microwave
filtrationthe precipitated solid was filtered off
washwashed with water
custombefore being recrystallised from ethanol (twice)

Sources & evidence

ORD record: ord-f9704ecec23d46a385f9603f77dcd32f
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09180122B2

Reaction notes

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