2,3-Dimethoxy-5-(2-phenylethyl)pyridine → 3-Hydroxy-5-(2-Phenylethyl)pyridin-2(1h)-One

HRID 709081Notes

Reaction equation

HRID 709081 reaction equation
[OH:1][C:2]1[C:3](=[O:17])[NH:4][CH:5]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2C)[CH:7]=1.COC1C(OC)=CC(CCC2C=CC=CC=2)=CN=1>>[OH:1][C:2]1[C:3](=[O:17])[NH:4][CH:5]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 711858192,3-Dimethoxy-5-(2-phenylethyl)pyridine2×HCID 711871703-hydroxy-5-(2-methylphenethyl)pyridin-2(1H)-one

Product 1

HCID 711871813-Hydroxy-5-(2-Phenylethyl)pyridin-2(1h)-OneYield 16%

Procedure

Prepared as described for 3-Hydroxy-5-(2-methylphenethyl)pyridin-2(1H)-one (Example 26) from 2,3-dimethoxy-5-(2-phenylethyl)pyridine (Intermediate 6). Purification by column chromatography (C18-SiO2; 5-95% methanol in water with 0.01% formic acid) gave 3-hydroxy-5-(2-phenylethyl)pyridin-2(1H)-one as a purple solid (10 mg, 16%).

Workup

  1. customPrepared
  2. customPurification by column chromatography (C18-SiO2; 5-95% methanol in water with 0.01% formic acid)

Sources & evidence

ORD record
ord-f92198b9374144de9729ee9ad869d055
Source dataset
uspto-grants-2015_11
Patent number
US09180122B2

Reaction notes

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