4-Isopropyl-2-nitrobenzoic acid → 2-Amino-4-isopropylbenzoic acid

HRID 605381Notes

Reaction equation

HRID 605381 reaction equation
[CH:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([N+:13]([O-])=O)[CH:5]=1)([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[NH2:13][C:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 249719544-Isopropyl-2-nitrobenzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 670403622-Amino-4-isopropylbenzoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The product of Example 431C (0.697 g, 3.332 mmol) was hydrogenated in methanol (30 mL) with 10% palladium-on-carbon (70 mg) at 1 atmosphere hydrogen pressure (balloon) for 2 hours. The reaction was filtered through a 0.45 micron PTFE membrane and the catalyst thoroughly washed with methanol. The filtrate was concentrated by rotary evaporation to give the title compound (0.585 g, 3.264 mmol, 98%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.15 (d, J=6.62 Hz, 6 H) 2.61-2.92 (m, 1 H) 6.41 (dd, J=8.46, 1.47 Hz, 1 H) 6.58 (d, J=1.84 Hz, 1 H) 7.60 (d, J=8.46 Hz, 1 H) 8.46 (br s, 2 H); MS (ESI+) m/z 180 (M+H)+.

Workup

  1. filtrationThe reaction was filtered through a 0.45 micron PTFE membrane
  2. washthe catalyst thoroughly washed with methanol
  3. concentrationThe filtrate was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-372f8bcc8d9148a699c4b73cd3222345
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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