HCID 19430580, compound → HCID 19430588, compound

HRID 2399289Notes

Reaction equation

HRID 2399289 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[C:8]([C:10]([CH3:14])([CH3:13])[CH2:11][CH3:12])[CH:7]=[CH:6][C:5]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=1[N+:26]([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:26][C:17]1[CH:18]=[C:19]([C:22]([F:23])([F:24])[F:25])[CH:20]=[CH:21][C:16]=1[O:15][C:5]1[CH:6]=[CH:7][C:8]([C:10]([CH3:13])([CH3:14])[CH2:11][CH3:12])=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:29]

Participants

4

Reactant 1

HCID 19430580HCID 19430580, compound

Product 1

HCID 19430588HCID 19430588, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl-2-(nitro-4-trifluoromethylphenoxy)-5-(1,1-dimethylpropyl)benzoate (2.5 g, 0.006 mol) was mixed in ethyl acetate (50 mL) and a palladium on carbon catalyst (600 mg) was added under argon. This mixture was hydrogenated at 50 psi for 3 h. The mixture was filtered through Celite® and washed with methanol and ethyl acetate. The solvents were evaporated to yield the title compound. 1H NMR (250 MHz, CDCl3) δ7.84 (d, 1H), 7.44 (dd, 1H), 7.03 (d, 1H), 684-6.97 (m, 2H), 6.72 (d, 1H), 4.22 (s, 2H), 3.81 (s, 3H), 1.55-1.72 (m, 2H), 1.29 (s, 6H), 0.60-0.77 (t, 3H).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washwashed with methanol and ethyl acetate
  3. customThe solvents were evaporated

Sources & evidence

ORD record
ord-332e975f2b0449d1834565f8bd4b6803
Source dataset
uspto-grants-1995_09
Patent number
US05447957

Reaction notes

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