4-(4-methoxy-3-nitro-phenyl)-3,6-dihydro-2H-pyran → 2-Methoxy-5-(tetrahydropyran-4-yl)-phenylamine

HRID 1244381Notes

Reaction equation

HRID 1244381 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][O:12][CH2:13][CH:14]=2)=[CH:5][C:4]=1[N+:15]([O-])=O>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][C:4]=1[NH2:15]

Participants

4

Reactant 1

HCID 219192154-(4-methoxy-3-nitro-phenyl)-3,6-dihydro-2H-pyran

Product 1

HCID 219192622-Methoxy-5-(tetrahydropyran-4-yl)-phenylamineYield 71.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.3 g 4-(4-Methoxy-3-nitro-phenyl)-3,6-dihydro-2H-pyran (5.5 mmol) was dissolved in ethanol (100 ml) and treated with Pd/C 10% (0.065 g) under an atmosphere of hydrogen for 16 h. After filtration, evaporation and drying of the residue, 0.82 g of 2-methoxy-5-(tetrahydro-pyran-4-yl)-phenylamine (71%) were obtained as an off-white solid; M.p.: 102–103° C.

Workup

  1. filtrationAfter filtration, evaporation
  2. customdrying of the residue

Sources & evidence

ORD record
ord-9790bddbf5c644399d506d4a05476396
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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