HCID 131732467, compound → HCID 131736039, compound

HRID 1049720Notes

Reaction equation

HRID 1049720 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[CH:24]=[CH:23][C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:16]=2[N+:25]([O-])=O)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.CO.[C].[Pd]>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]2[CH:24]=[CH:23][C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[C:16]=2[NH2:25])=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 131732467HCID 131732467, compound

Product 1

HCID 131736039HCID 131736039, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl[4-[(1-nitro-5,6,7,8-tetrahydro-2-naphthyl)amino]phenyl]carbamate (7.66 g, 20 mmol) was dissolved in tetrahydrofuran (77 mL) and methanol (77 mL), the solution was added with 10% palladium-carbon (0.77 g), and the mixture was stirred at room temperature for 42 hours under a hydrogen atmosphere. The catalyst was separated by filtration, then the solvent was evaporated under reduced pressure, and the residue was washed with hexane to obtain the title compound (6.71 g, yield 95%) as pale brown crystals.

Workup

  1. customThe catalyst was separated by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. washthe residue was washed with hexane

Sources & evidence

ORD record
ord-62fb0e8da0324ce19f5d594314239ca0
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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