5'-Isopropyl-5,2'-dimethoxy-2-nitro-4-trifluoromethyl-biphenyl → 5'-Isopropyl-5,2'-dimethoxy-4-trifluoromethyl-biphenyl-2-ylamine

HRID 604176Notes

Reaction equation

HRID 604176 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:25][CH3:26])=[C:8]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([C:18]([F:21])([F:20])[F:19])=[CH:12][C:11]=2[N+:22]([O-])=O)[CH:9]=1)([CH3:3])[CH3:2]>O1CCCC1.CO.[C].[Pd]>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:25][CH3:26])=[C:8]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([C:18]([F:19])([F:21])[F:20])=[CH:12][C:11]=2[NH2:22])[CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 666031075'-Isopropyl-5,2'-dimethoxy-2-nitro-4-trifluoromethyl-biphenyl

Product 1

HCID 666033195'-Isopropyl-5,2'-dimethoxy-4-trifluoromethyl-biphenyl-2-ylamineYield 87.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5′-Isopropyl-5,2′-dimethoxy-2-nitro-4-trifluoromethyl-biphenyl (2.35 g) is dissolved in a mixed solvent of tetrahydrofuran (20 ml) and methanol (30 ml), and thereto is added 10% palladium-carbon (500 mg) and the mixture is stirred under hydrogen atmosphere at room temperature for 1 day. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1) to give 5′-isopropyl-5,2′-dimethoxy-4-trifluoromethyl-biphenyl-2-ylamine (1.88 g). MS (m/z): 340 [M+H]+

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1)

Sources & evidence

ORD record
ord-b6c5bd9af8a24e9f941ae2cfdc160364
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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