2-Ethoxy-5-nitro-1,3-bis(trifluoromethyl)benzene → HCID 86666596, compound

HRID 62720Notes

Reaction equation

HRID 62720 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][C:7]([N+:14]([O-])=O)=[CH:6][C:5]=1[C:17]([F:20])([F:19])[F:18])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]1[C:5]([C:17]([F:18])([F:19])[F:20])=[CH:6][C:7]([NH2:14])=[CH:8][C:9]=1[C:10]([F:11])([F:12])[F:13])[CH3:2]

Participants

4

Reactant 1

HCID 866665952-Ethoxy-5-nitro-1,3-bis(trifluoromethyl)benzene

Product 1

HCID 86666596HCID 86666596, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

2-Ethoxy-5-nitro-1,3-bis(trifluoromethyl)benzene (2) (1.00 g, 3.30 mmol) was dissolved in MeOH (150 mL) and passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 30° C. under H2 (full H2 mode). The solvent was removed in vacuo and the residue was dissolved in EtOH (20 mL) and then treated with 10% Pd/C (182 mg, 171 μmol). Hydrogen gas was bubbled through the mixture, with stirring at RT for 2 h. The mixture was then filtered through Celite and concentrated in vacuo. The residue was purified by silica gel chromatography (15% EtOAc in isohexane) to afford 4-ethoxy-3,5-bis(trifluoromethyl)aniline (3) (460 mg, 56%) as a white solid: m/z 273 [M+H]+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.09 (2H, s), 5.76 (2H, s), 3.87 (2H, q), 1.29 (3H, t).

Workup

  1. customat 30° C.
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in EtOH (20 mL)
  4. customHydrogen gas was bubbled through the mixture
  5. filtrationThe mixture was then filtered through Celite
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (15% EtOAc in isohexane)

Sources & evidence

ORD record
ord-9887b94bb185481485389b06d8cc2e2b
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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