HCID 19430580, compound → HCID 19430588, compound

HRID 1077986Notes

Reaction equation

HRID 1077986 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-d9f061c9a58d4782a5f6af627f7f78fd
Source dataset
uspto-grants-1996_08
Patent number
US05545669

Reaction notes

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