4-Methyl-5-[3-trifluoromethylphenoxy]-6-methoxy-8-nitroquinoline → 4-Methyl-5-(3-trifluoromethylphenoxy)-6-methoxy-8-aminoquinoline

HRID 1388566Notes

Reaction equation

HRID 1388566 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([N+:25]([O-])=O)[CH:8]=[C:9]([O:23][CH3:24])[C:10]=2[O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[N:5]=[CH:4][CH:3]=1>[Ni]>[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([NH2:25])[CH:8]=[C:9]([O:23][CH3:24])[C:10]=2[O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=2)[N:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 6332094-Methyl-5-[3-trifluoromethylphenoxy]-6-methoxy-8-nitroquinoline

Product 1

HCID 130042034-Methyl-5-(3-trifluoromethylphenoxy)-6-methoxy-8-aminoquinolineYield 76%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A solution of 4-methyl-5-(3-trifluoromethylphenoxy) -6-methoxy-8-nitroquinoline (VI, 5.9 g, 15.6 mmol) in ethanol-dioxane (4:3, v/v, 350 mL) containing wet Raney nickel (ca. 4 g) was reduced at 45 psig for 11/4 hour. The catalyst was filtered and the filtrate was concentrated to dryness. The residual solid was crystallized from ligroin (bp 60°-80°) to afford 4.1 g (76%) of the title compound mp 113°-115°. A sample recrystallized once again gave an analytical sample, mp 116°-117°.

Workup

  1. custom4 hour
  2. filtrationThe catalyst was filtered
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe residual solid was crystallized from ligroin (bp 60°-80°)

Sources & evidence

ORD record
ord-f142b163c9734b639e274dc2e042ce0d
Source dataset
uspto-grants-1984_02
Patent number
US04431807

Reaction notes

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