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

HRID 1582103Notes

Reaction equation

HRID 1582103 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>CO.ClCCl.[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

5

Reactant 1

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

Product 1

HCID 219192622-Methoxy-5-(tetrahydropyran-4-yl)-phenylamineYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3.30 g (14.0 mmol) 4-(4-methoxy-3-nitro-phenyl)-3,6-dihydro-2H-pyran in 70 ml methanol and 70 ml dichloromethane was added a spatula end of 10% palladium on charcoal and the mixture was then stirred for 20 minutes at room temperature under an atmosphere of hydrogen. The mixture was then filtered, washing with dichloromethane, and the filtrate concentrated in vacuo to afford 2.75 g (95%) 2-methoxy-5-(tetrahydro-pyran-4-yl)-phenylamine as an off-white crystalline solid. ES-MS m/e (%): 208 (M+H+, 100).

Workup

  1. filtrationThe mixture was then filtered
  2. washwashing with dichloromethane
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-68bc5d73fe5f42508c8cd2b1b6f0b42f
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

Loading…