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

HRID 2390457Notes

Reaction equation

HRID 2390457 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 (200 mL) at 120° C. for 18 h and then concentrated. The residue was dissolved in MeOH (100 mL) and made basic with 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 (289 mg, 89%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 11.08 (s, 1H) 9.10 (s, 1H), 8.36-8.33 (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. 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-597cb19a7c1146b783f4fefb98a5ca75
Source dataset
uspto-grants-2012_09
Patent number
US08273770B2

Reaction notes

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