N-(2-chloro-4-hydroxy-6-nitrophenyl)tetrahydro-2H-pyran-4-carboxamide → N-(2-amino-6-chloro-4-hydroxyphenyl)tetrahydro-2H-pyran-4-carboxamide

HRID 1846495Notes

Reaction equation

HRID 1846495 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[NH:12][C:13]([CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14].[H][H]>C(OCC)(=O)C.[Ni]>[NH2:9][C:4]1[CH:5]=[C:6]([OH:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[NH:12][C:13]([CH:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)=[O:14]

Participants

5

Reactant 2

HCID 66978264N-(2-chloro-4-hydroxy-6-nitrophenyl)tetrahydro-2H-pyran-4-carboxamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 66978316N-(2-amino-6-chloro-4-hydroxyphenyl)tetrahydro-2H-pyran-4-carboxamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

0.60 g (2.00 mmol) N-(2-chloro-4-hydroxy-6-nitrophenyl)tetrahydro-2H-pyran-4-carboxamide were placed in 10 mL ethyl acetate and hydrogenated under a hydrogen atmosphere and with the addition of 0.20 g Raney nickel at RT and a hydrogen pressure of 3 bar until all the hydrogen had been taken up. The catalyst was filtered off and the filtrate was evaporated down i.vac.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated down i.vac

Sources & evidence

ORD record
ord-7d3c95963aae4638b93c4bb35a361329
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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