Nitromethane → 2-[4-(2-Nitro-vinyl)-phenoxy]-5-trifluoromethyl-pyridine

HRID 474729Notes

Reaction equation

HRID 474729 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)=[N:7][CH:8]=1.C([O-])(=O)C.[NH4+].[N+:25]([CH3:28])([O-:27])=[O:26]>>[N+:25]([CH:28]=[CH:14][C:13]1[CH:16]=[CH:17][C:10]([O:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:19])([F:18])[F:1])=[CH:8][N:7]=2)=[CH:11][CH:12]=1)([O-:27])=[O:26]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 269857004-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}benzaldehyde

Product 1

HCID 677734032-[4-(2-Nitro-vinyl)-phenoxy]-5-trifluoromethyl-pyridineYield 56%

Conditions

Temperature
95 °C

Procedure

Entire reaction was performed under argon using syringe septa technique. 4-(5-trifluoromethyl-pyridin-2-yloxy)-benzaldehyde (2.170 mmol, 1 eq) and ammonium acetate (1.736 mmol, 0.8 eq) were dissolved in nitromethane (3 ml) and reaction mixture was stirred at 95° C. overnight. The volatile was removed in vacuo and the residue was partitioned between DCM and water. Organic layers were combined, washed with brine, dried over MgSO4, filtered and evaporated giving 2-[4-(2-nitro-vinyl)-phenoxy]-5-trifluoromethyl-pyridine (1.225 mmol, yield=56%, purity=95%). [M+H]+=311.23 1H NMR (300 MHz, DMSO-d6) δ/ppm 7.27-7.36 (m, 3H), 7.91-7.98 (m, 2H), 8.24-8.30 (m, 1H), 8.55-8.62 (m, 1H)

Workup

  1. customEntire reaction
  2. customreaction mixture
  3. customThe volatile was removed in vacuo
  4. customthe residue was partitioned between DCM and water
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-ddce3fa050d4485cb36f6466b6fe33d4
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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