2-(5-(3,4-dimethoxy-5-nitrophenyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)pyridine → 3-nitro-5-(1-(5-(trifluoromethyl)pyridin-2-yl)-1H-imidazol-5-yl)benzene-1,2-diol

HRID 42651Notes

Reaction equation

HRID 42651 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:14]2[N:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=3)[CH:17]=[N:16][CH:15]=2)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9]C>Br>[N+:11]([C:7]1[CH:6]=[C:5]([C:14]2[N:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=3)[CH:17]=[N:16][CH:15]=2)[CH:4]=[C:3]([OH:2])[C:8]=1[OH:9])([O-:13])=[O:12]

Participants

3

Reactant 1

HCID 687019682-(5-(3,4-dimethoxy-5-nitrophenyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)pyridine

Product 1

HCID 687064483-nitro-5-(1-(5-(trifluoromethyl)pyridin-2-yl)-1H-imidazol-5-yl)benzene-1,2-diol

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

2-(5-(3,4-dimethoxy-5-nitrophenyl)-1H-imidazol-1-yl)-5-(trifluoromethyl)pyridine (0.394 g, 1 mmol) was heated at 140° C. in 48% aqueous hydrogen bromide (6 mL) for 2.5 hours. The dark homogeneous solution was cooled to room temperature and volatiles were removed by evaporation to leave a pale brown crystalline solid that was dried over P2O5 under vacuum. Trituration of the resulting solid with diethyl ether gave 3-nitro-5-(1-(5-(trifluoromethyl)pyridin-2-yl)-1H-imidazol-5-yl)benzene-1,2-diol as a yellow crystalline solid, 0.263 g (72%).

Workup

  1. customvolatiles were removed by evaporation
  2. customto leave a pale brown crystalline solid
  3. dry with materialthat was dried over P2O5 under vacuum

Sources & evidence

ORD record
ord-a850b11ac09c40488da4a411403e8af2
Source dataset
uspto-grants-2013_09
Patent number
US08536203B2

Reaction notes

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