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 1081296Notes

Reaction equation

HRID 1081296 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.[H][H]>O1CCCC1>[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 2

HCID 538772305-Nitro-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxoleHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

57.4 g of the product from Example 15a were dissolved in 400 ml of tetrahydrofuran and hydrogenated in the presence of 4 g of catalyst (palladium on carbon, 10% by weight) for 5 hours at 30° C. at 50 bar with hydrogen. 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-1ba835f74877438b9fdc4916160febb3
Source dataset
uspto-grants-1996_12
Patent number
US05585395

Reaction notes

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