Trimethylamine → 3-Amino-5-methylbenzotrifluoride

HRID 371506Notes

Reaction equation

HRID 371506 reaction equation
Cl[CH:2](Cl)[C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[C:5]([C:12]([F:15])([F:14])[F:13])[CH:4]=1.CN(C)C.[H][H]>[Pd].CO>[CH3:2][C:3]1[CH:4]=[C:5]([C:12]([F:13])([F:14])[F:15])[CH:6]=[C:7]([NH2:9])[CH:8]=1

Participants

6

Reactant 3

HCID 1146TrimethylamineHCID 20273455HCID 20273455, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 27377133-Amino-5-methylbenzotrifluorideYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

At room temperature, 32.3 gms of crude nitrated product from Example V was added to a mixture of 150 ml MeOH and 30 gms (2.5 eq) of trimethylamine. The dark solution was charged with 1.6 gms of 50% wet 5% Pd/C catalyst and hydrogenated for 48 hours at 60° C. with hydrogen at 4 atms. The final solution was concentrated by distilling about half of the MeOH, diluted with 250 ml H2O and washed 3 times with 100 ml CH2Cl2. All of the organic extractions were combined, dried (Na2SO4), filtered and concentrated to 24 gms of a dark liquid which was Kugelrohr distilled at 95°-110° C./32 mm to 17.6 gms of light yellow colored crystals of 3-methyl-5-amino benzotrifluoride; mp 27°-28° C. (83% yield).

Workup

  1. concentrationThe final solution was concentrated
  2. distillationby distilling about half of the MeOH
  3. additiondiluted with 250 ml H2O
  4. washwashed 3 times with 100 ml CH2Cl2
  5. extractionAll of the organic extractions
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to 24 gms of a dark liquid which
  9. distillationdistilled at 95°-110° C./32 mm to 17.6 gms of light yellow colored crystals of 3-methyl-5-amino benzotrifluoride

Sources & evidence

ORD record
ord-b0247f3e3bb1420c83818ccbf67ffb35
Source dataset
uspto-grants-1985_07
Patent number
US04532353

Reaction notes

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