Methanol → tert-Butyl[2-[(1-amino-2-naphthyl)amino]ethyl]carbamate

HRID 1049734Notes

Reaction equation

HRID 1049734 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][NH:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]=1[N+:21]([O-])=O)([CH3:4])([CH3:3])[CH3:2].CO>O1CCCC1.[Pt]=O>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][NH:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]=1[NH2:21])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 887MethanolHCID 131736041HCID 131736041, compound

Product 1

HCID 131736042tert-Butyl[2-[(1-amino-2-naphthyl)amino]ethyl]carbamateYield 95.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl[2-[(1-nitro-2-naphthyl)amino]ethyl]carbamate (746 mg, 2.25 mmol) was dissolved in tetrahydrofuran (7.5 mL), and methanol (7.5 mL), the solution was added with platinum oxide (7.5 mg), and the mixture was stirred at room temperature for 7 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 give the title compound (646 mg, yield 95%) as 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-38bb2893774449e0bcdd51a5cad4825f
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

Loading…