Tert-butyl {2-chloro-5-[(6-nitropyridin-3-yl)oxy]phenyl}carbamate → Tert-butyl {5-[(6-aminopyridin-3-yl)oxy]-2-chlorophenyl}carbamate

HRID 1874373Notes

Reaction equation

HRID 1874373 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=2)=[CH:4][C:3]=1[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]>CO.[C].[Pd]>[NH2:15][C:12]1[N:11]=[CH:10][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH:4]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 57749305Tert-butyl {2-chloro-5-[(6-nitropyridin-3-yl)oxy]phenyl}carbamate

Product 1

HCID 57749356Tert-butyl {5-[(6-aminopyridin-3-yl)oxy]-2-chlorophenyl}carbamateYield 59%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl {2-chloro-5-[(6-nitropyridin-3-yl)oxy]phenyl}carbamate (13.5 g, 36.9 mmol) in methanol (500 mL) was added palladium carbon (50% water-containing product, 2.96 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 17 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, hexane/ethyl acetate=100/0→75/25) to give the title compound (7.29 g, 59%) as a pale-yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=100/0→75/25)

Sources & evidence

ORD record
ord-2b3c2fcb0a664a5badbe9d02c0b9e86c
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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