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 37577Notes

Reaction equation

HRID 37577 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 of Example 27 were dissolved in 400 ml of tetrahydrofuran and hydrogenated with hydrogen at 50 bar for 5 hours at 30° C. in the presence of 4 g of catalyst (palladium-on-charcoal, 10% by weight). After filtration, the solvent was removed and the residue was distilled under high vacuum to give 37 g of product (=63% of theory) 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. filtrationAfter filtration
  2. customthe solvent was removed
  3. distillationthe residue was distilled under high vacuum

Sources & evidence

ORD record
ord-328aebc08e5c4b5fb930e3ddca84d0e8
Source dataset
uspto-grants-1995_05
Patent number
US05420309

Reaction notes

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