Trimethylamine → 3-Amino-5-methylbenzotrifluoride

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).

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

ORD-Eintrag

ord-b0247f3e3bb1420c83818ccbf67ffb35

Quelldatensatz

uspto-grants-1985_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04532353