Methyl 2-methyl-3-nitro-5-(trifluoromethyl)benzoate → Methyl 3-amino-2-methyl-5-(trifluoromethyl)benzoate

HRID 2208662Notes

Reaction equation

HRID 2208662 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:9]([C:15]([F:18])([F:17])[F:16])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CO.[OH-].[OH-].[Pd+2]>[NH2:12][C:11]1[C:2]([CH3:1])=[C:3]([CH:8]=[C:9]([C:15]([F:16])([F:17])[F:18])[CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 68295416Methyl 2-methyl-3-nitro-5-(trifluoromethyl)benzoate

Product 1

HCID 68295733Methyl 3-amino-2-methyl-5-(trifluoromethyl)benzoateYield 58%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 2-methyl-3-nitro-5-(trifluoromethyl)benzoate (20.0 g, 76.0 mmol) in MeOH (400 ml) was added Pd(OH)2 (2.00 g). The reaction mixture was stirred for 3 hours under hydrogen atmosphere. After purging with nitrogen, the mixture was filtered and the filtrate was concentrated in vacuo to give the titled compound as an orange solid (10.2 g, 58% yield). 1H-NMR (400 MHz, CDCl3) δppm; 7.47 (brs, 1H), 7.01 (d, J=2.0 Hz, 1H), 3.92 (m, 2H), 3.91 (s, 3H), 2.39 (s, 3H).

Workup

  1. customAfter purging with nitrogen
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-658a44db49f344bea40bd0700e2cd23d
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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