6-Methyl-5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinolin-l-amine → 6-methyl-N1-(3-(trifluoromethyl)phenyl)isoquinoline-1,5-diamine

HRID 2092271Notes

Reaction equation

HRID 2092271 reaction equation
[CH3:1][C:2]1[C:3]([N+:23]([O-])=O)=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)=[N:7][CH:6]=[CH:5]2>C(O)C.[Pd]>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:20])[F:21])[CH:14]=3)=[N:7][CH:6]=[CH:5][C:4]=2[C:3]=1[NH2:23]

Participants

4

Reactant 1

HCID 673394766-Methyl-5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinolin-l-amine

Product 1

HCID 444789036-methyl-N1-(3-(trifluoromethyl)phenyl)isoquinoline-1,5-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-Methyl-5-nitro-N-(3-(trifluoromethyl)phenyl)isoquinolin-l-amine (0.28 g, 0.81 mmol) was disolved in ethanol (20 mL) and 10% palladium on carbon (0.086 g, 0.81 mmol) was added to the solution. The reaction stirred overnight at RT under a hydrogen atmosphere. The reaction was filtered through celite and concentrated to give the title compound as a pink film (0.25 g, 98%). MS (M+H)+ 318.

Workup

  1. filtrationThe reaction was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7e0b0e2d37804a53899aacef38cf1183
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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