2'Methoxy-5-(trifluoromethyl)-2,4'-bipyridine → 4-(5-(Trifluoromethyl)pyridin-2-yl)pyridin-2(1H)-one

HRID 1521469Notes

Reaction equation

HRID 1521469 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][N:10]=2)[CH:6]=[CH:5][N:4]=1>Cl>[F:18][C:15]([F:16])([F:17])[C:12]1[CH:13]=[CH:14][C:9]([C:7]2[CH:6]=[CH:5][NH:4][C:3](=[O:2])[CH:8]=2)=[N:10][CH:11]=1

Participants

3

Reactant 1

HCID 575147602'Methoxy-5-(trifluoromethyl)-2,4'-bipyridine

Product 1

HCID 576255234-(5-(Trifluoromethyl)pyridin-2-yl)pyridin-2(1H)-oneYield 91.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2′-Methoxy-5-(trifluoromethyl)-2,4′-bipyridine (337 mg, 1.32 mmol) was stirred in concentrated hydrochloric acid (20 mL) at 120° C. for 18 h and then concentrated. The residue was adjusted to pH 8 with 6 N NaOH, and the solids were filtered off, washed with water and dried under vacuum to provide the title compound (289 mg, 89%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 11.08 (s, 1H) 9.10 (s, 1H), 8.35 (dd, J=8.4, 2.1 Hz, 1H), 8.25 (d, J=8.3 Hz, 1H), 7.53 (d, J=6.8, 1H), 7.09 (d, J=1.3 Hz, 1H), 6.90 (dd, J=6.8, 1.6 Hz, 1H).

Workup

  1. concentrationconcentrated
  2. filtrationthe solids were filtered off
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b6e428d3cad544f9933395fd5bfbc467
Source dataset
uspto-grants-2015_07
Patent number
US09073925B2

Reaction notes

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