Potassium Formate → Ethyl 2-(4-aminophenyl)-2-methylpropanoate

HRID 74083Notes

Reaction equation

HRID 74083 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)([O-])=O.C([O-])=O.[K+]>CCO.O.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]([CH3:16])([CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 2735122Potassium FormateHCID 15544079Ethyl 2-methyl-2-(4-nitrophenyl)propanoate

Product 1

HCID 15544083Ethyl 2-(4-aminophenyl)-2-methylpropanoateYield 85.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A solution of ethyl 2-(4-nitrophenyl)-2-methylpropanoate (900 mg, 3.8 mmol) in EtOH (10 mL) was treated with 10% Pd—C (80 mg) and heated to 45° C. A solution of potassium formate (4.10 g, 48.8 mmol) in H2O (11 mL) was added over a period of 15 min. The reaction mixture was stirred at 65° C. for 2 h and then treated with additional 300 mg of Pd/C. The reaction was stirred for 1.5 h and then filtered through Celite. The solvent volume was reduced by approximately 50% under reduced pressure and extracted with EtOAc. The organic layers were dried over Na2SO4 and the solvent was removed under reduced pressure to yield ethyl 2-(4-aminophenyl)-2-methylpropanoate (G-1) (670 mg, 85%). 1H NMR (400 MHz, CDCl3) δ 7.14 (d, J=8.5 Hz, 2H), 6.65 (d, J=8.6 Hz, 2H), 4.10 (q, J=7.1 Hz, 2H), 1.53 (s, 6H), 1.18 (t, J=7.1 Hz, 3H).

Workup

  1. stirringThe reaction was stirred for 1.5 h
  2. filtrationfiltered through Celite
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layers were dried over Na2SO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0fb9aa8c8393480bb565697a4165ab56
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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