Potassium Formate → Methyl 2-tert-butyl-5-aminobenzoate

HRID 74074Notes

Reaction equation

HRID 74074 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:6]=1[C:7]([O-:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH:17]([O-])=O.[K+]>CCO.O.[Pd]>[C:1]([C:5]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:6]=1[C:7]([O:9][CH3:17])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 2735122Potassium FormateHCID 283640992-Tert-butyl-5-nitrobenzoate

Product 1

HCID 57470263Methyl 2-tert-butyl-5-aminobenzoateYield 96.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a refluxing solution of 2-tert-butyl-5-nitrobenzoate (90 mg, 0.38 mmol) in EtOH (2.0 mL) was added potassium formate (400 mg, 4.76 mmol) in water (1 mL), followed by the addition of 20 mg of 10% Pd—C. The reaction mixture was refluxed for additional 40 min, cooled to room temperature and filtered through Celite. The filtrate was concentrated to give methyl 2-tert-butyl-5-aminobenzoate (E-6) (76 mg, 95%), which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.24 (d, J=8.6 Hz, 1H), 6.67 (dd, J=8.6, 2.7 Hz, 1H), 6.60 (d, J=2.7 Hz, 1H), 3.86 (s, 3H), 1.34 (s, 9H); HPLC ret. time 2.19 min, 10-99% CH3CN, 5 min run; ESI-MS 208.2 m/z (MH+).

Workup

  1. temperatureThe reaction mixture was refluxed for additional 40 min
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-438a69d55e1942ba9953fe4d639b0dae
Source dataset
uspto-grants-2014_09
Patent number
US08829204B2

Reaction notes

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