HCID 19387388, compound → HCID 19387380, compound

HRID 2399293Notes

Reaction equation

HRID 2399293 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=1[N+:23]([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:23][C:14]1[CH:15]=[C:16]([C:19]([F:20])([F:21])[F:22])[CH:17]=[CH:18][C:13]=1[O:12][C:5]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:26]

Participants

4

Reactant 1

HCID 19387388HCID 19387388, compound

Product 1

HCID 19387380HCID 19387380, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl-2-(nitro-4-trifluoromethylphenoxy)-4-methoxybenzoate (21.65 g 0.058 mol) was dissolved in ethyl acetate and a palladium on carbon catalyst was added under argon. The mixture was hydrogenated in a parr bottle, at 50 psi, for 4 h The mixture was filtered through Celite® and washed with ethyl acetate and methanol. The solvent was evaporated and the residue flash chromatographed (silica gel, ethyl acetate/hexane) to yield the title compound. 1H NMR (250 MHz, CDCl3) δ7.92 (d, 1H), 7.03 (d, 1H) 6.90 (dd, 1H) 6.68-6.81 (m, 2H) 6.50 (d, 1H) 4.22 (s, 2H) 3.75 (s, 6H).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washwashed with ethyl acetate and methanol
  3. customThe solvent was evaporated
  4. customthe residue flash chromatographed (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0f830c0683c74e909ed5bf882599ef68
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

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