Methanol → 2-Methoxy-5-(trifluoromethyl)benzene-1,3-diamine

HRID 985461Notes

Reaction equation

HRID 985461 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][C:6]([C:12]([F:15])([F:14])[F:13])=[CH:5][C:4]=1[N+:16]([O-])=O.CO.C([O-])=O.[NH4+]>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([C:12]([F:13])([F:15])[F:14])=[CH:5][C:4]=1[NH2:16]

Participants

6

Reactant 3

HCID 887MethanolHCID 2723923Ammonium formateHCID 28040782-Methoxy-1,3-dinitro-5-(trifluoromethyl)benzene

Product 1

HCID 225069942-Methoxy-5-(trifluoromethyl)benzene-1,3-diamineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Methoxy-1,3-dinitro-5-trifluoromethylbenzene (3.0 g, 11.3 mmol) was dissolved in 100 mL 50:50 EtOAc:MeOH. Ammonium formate (7.06 g, 112 mmol) was added followed by palladium-on-carbon catalyst (1.0 g). The reaction was heated to a gentle reflux for 45 min, then allowed to cool, and filtered through a plug of diatomaceous earth. The calalyst was washed with EtOAc repeatedly, and the filtrate was in vacuo. The residue was taken up in 500 ml 50% EtOAc in hexanes and filtered through a short plug of silica gel. The filtrate was concentrated in vacuo, providing 2.15 g (10.4 mmol, 95%) of 2-methoxy-5-trifluoromethyl-benzene-1,3-diamine as a brown oil.

Workup

  1. temperatureThe reaction was heated to
  2. temperaturea gentle reflux for 45 min
  3. temperatureto cool
  4. filtrationfiltered through a plug of diatomaceous earth
  5. washThe calalyst was washed with EtOAc repeatedly
  6. filtrationfiltered through a short plug of silica gel
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-86aa55a1b7e44386abc086fc67d02bc6
Source dataset
uspto-grants-2005_03
Patent number
US06872726B2

Reaction notes

Loading…