2-(2,4-Dinitro-phenyl)-3,3,3-trifluoro-2-trifluoromethyl-propionic acid methyl ester → 6-Amino-1-hydroxy-3,3-bis-trifluoromethyl-1,3-dihydro-indol-2-one

HRID 887602Notes

Reaction equation

HRID 887602 reaction equation
C[O:2][C:3](=O)[C:4]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=1[N+:22]([O-])=[O:23])([C:9]([F:12])([F:11])[F:10])[C:5]([F:8])([F:7])[F:6]>CCO.[Pd]>[NH2:19][C:16]1[CH:15]=[C:14]2[C:13]([C:4]([C:9]([F:12])([F:10])[F:11])([C:5]([F:8])([F:7])[F:6])[C:3](=[O:2])[N:22]2[OH:23])=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 865887022-(2,4-Dinitro-phenyl)-3,3,3-trifluoro-2-trifluoromethyl-propionic acid methyl ester

Product 1

HCID 219614506-Amino-1-hydroxy-3,3-bis-trifluoromethyl-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To an argon-degassed solution of 5.13 g (13.64 mmol) 2-(2,4-dinitro-phenyl)-3,3,3-trifluoro-2-trifluoromethyl-propionic acid methyl ester in 300 ml EtOH was added 0.5 g of 10% by weight Pd/C. The reaction was stirred under H2 overnight and filtered through Celite®, concentrated down, and dried under vacuum, yielding the titled compound.

Workup

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated down
  3. customdried under vacuum

Sources & evidence

ORD record
ord-d88d2fe07f2741b1bb8ec22bd981aa36
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

Loading…