N-methyl-2-pyrrolidone → Tert-butyl {3-[(5-aminopyridin-2-yl)oxy]-4-methylphenyl}carbamate

HRID 1800502Notes

Reaction equation

HRID 1800502 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][N:18]=1.CN1CCCC1=O>CO.[C].[Pd]>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:3]2[CH:4]=[C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH:6]=[CH:7][C:2]=2[CH3:1])=[N:18][CH:19]=1

Participants

5

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 86646009Tert-butyl {4-methyl-3-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate

Product 1

HCID 86646010Tert-butyl {3-[(5-aminopyridin-2-yl)oxy]-4-methylphenyl}carbamateYield 93.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl {4-methyl-3-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate (2.20 g, 6.37 mmol) in methanol (50 mL)/N-methylpyrrolidone (10 mL) was added 10% palladium-carbon powder (440 mg), and the mixture was stirred at room temperature for 4 hr under a hydrogen atmosphere (3.0 atm). 10% Palladium-carbon powder was filtered off by celite filtration, and water (20 mL) was added to the filtrate. The obtained precipitate was collected by filtration, and repeatedly washed with water to give the title compound (1.87 g, 93%) as a pale-gray powder.

Workup

  1. filtration10% Palladium-carbon powder was filtered off by celite filtration, and water (20 mL)
  2. additionwas added to the filtrate
  3. filtrationThe obtained precipitate was collected by filtration
  4. washrepeatedly washed with water

Sources & evidence

ORD record
ord-9f8a7468321c424593fd3795159861b7
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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