Ethyl Acetate → 2-isopropyl-5-methoxyaniline

HRID 1914706Notes

Reaction equation

HRID 1914706 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](O)([CH3:12])[CH3:11].CCOC(C)=O>CCO.[Pd]>[CH:10]([C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[NH2:1])([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 59352995HCID 59352995, compound

Product 1

HCID 593389572-isopropyl-5-methoxyanilineYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-(2-amino-4-methoxyphenyl)propan-2-ol (210 mg; 1.2 mmol; 1 eq) in a mixture of EtOH (10 mL), EtOAc (3 mL) and 5 N (1 mL) under nitrogen atmosphere is added palladium on charcoal (130 mg; 10%) and the reaction mixture is hydrogenated for 1 week at room temperature at 1 atmosphere. The catalyst is filtered through celite and the organic solvents are removed under vacuum. The residue is taken up in EtOAc. The organic phase is washed with a saturated aqueous solution of Na2CO3 and dried over MgSO4. The solvent is evaporated under reduced pressure to afford 160 mg (84%) of the title compound as a red oil. The compound is used in the next step without further purification. 1H NMR (DMSO-d6) δ 6.89 (d, J=9.0 Hz, 1H), 6.18 (d, J=3.0 Hz, 1H), 6.05 (dd, J=9.0, 3.0 Hz, 1H), 5.45-5.39 (m, 2H), 3.85 (s, 3H), 3.30-3.11 (m, 1H), 1.97 (s, 6H). HPLC (max plot) 70%; Rt 1.88 min.

Workup

  1. waitthe reaction mixture is hydrogenated for 1 week at room temperature at 1 atmosphere
  2. filtrationThe catalyst is filtered through celite
  3. customthe organic solvents are removed under vacuum
  4. washThe organic phase is washed with a saturated aqueous solution of Na2CO3
  5. dry with materialdried over MgSO4
  6. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-5638812308144f5fbda15c449c4b828b
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

Loading…