5-Nitro-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole → 5-Amino-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole

HRID 1417237Notes

Reaction equation

HRID 1417237 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[O:8][C:9]([CH2:15][C:16]([F:19])([F:18])[F:17])([C:11]([F:14])([F:13])[F:12])[O:10][C:6]=2[CH:5]=1)([O-])=O>O1CCCC1.[H][H]>[NH2:1][C:4]1[CH:21]=[CH:20][C:7]2[O:8][C:9]([CH2:15][C:16]([F:19])([F:18])[F:17])([C:11]([F:12])([F:13])[F:14])[O:10][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 538772305-Nitro-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole

Product 1

HCID 541715435-Amino-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxoleYield 71.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

57.4 g of the product from Example 15a were dissolved in 400 ml of tetrahydrofuran and hydrogenated with hydrogen in the presence of 4 g of catalyst (palladium on carbon, 10% by weight) at 30° C. for 5 hours and at 50 bar. The mixture was then filtered, the solvent removed, and the remaining filtrate distilled under a high vacuum. 37 g of product (=63% of theory) were obtained with a boiling point of 83° C. at 0.07 mbar. 19F-NMR: -59.0 and -84.6 ppm; 1H-NMR: 2.98 ppm.

Workup

  1. filtrationThe mixture was then filtered
  2. customthe solvent removed
  3. distillationthe remaining filtrate distilled under a high vacuum

Sources & evidence

ORD record
ord-c353e389f56942b8ba025dffd2aa2f50
Source dataset
uspto-grants-1999_03
Patent number
US05877195

Reaction notes

Loading…