2-Methoxy-4-phenethylpyridine → 4-(2-Phenylethyl)pyridin-2(1h)-one

HRID 1020555Notes

Reaction equation

HRID 1020555 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][N:4]=1>Cl>[CH2:9]([C:7]1[CH:6]=[CH:5][NH:4][C:3](=[O:2])[CH:8]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 579504422-Methoxy-4-phenethylpyridine

Product 1

HCID 2680294-(2-Phenylethyl)pyridin-2(1h)-oneYield 104.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-Methoxy-4-phenethylpyridine (22.0 g, 102 mmol) was stirred in concentrated hydrochloric acid (200 mL) at 120° C. for 18 h and then concentrated. The residue was dissolved in MeOH (100 mL) and made basic with aqueous 6 N NaOH and re-concentrated until most of the solvent had been removed. The solids were filtered off, washed with water and dried under vacuum to provide the title compound (21.3 g, 95%) as a beige solid: 1H NMR (500 MHz, DMSO-d6) δ 11.31 (br s, 1H), 7.28-7.21 (m, 5H), 7.17 (t, J=7.1 Hz, 1H), 6.10-6.08 (m, 2H), 2.85-2.82 (m, 2H), 2.70-2.67 (m, 2H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in MeOH (100 mL)
  3. concentrationre-concentrated until most of the solvent
  4. customhad been removed
  5. filtrationThe solids were filtered off
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-059b4559c06444518ff3058fbe2622a0
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

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