Methanol → 2-Methoxy-5-morpholinoaniline

HRID 2250794Notes

Reaction equation

HRID 2250794 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]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]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[CH:5][C:4]=1[NH2:15]

Participants

5

Reactant 2

HCID 887MethanolHCID 177470104-(4-Methoxy-3-nitrophenyl)morpholine

Product 1

HCID 113677782-Methoxy-5-morpholinoanilineYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

4-(4-Methoxy-3-nitro-phenyl)-morpholine (6 g) is hydrogenated in dichloromethane (100 ml) and methanol (600 ml) using palladium on carbon (10%, 600 mg) for 12 hours. The catalyst is removed by filtration and the solution evaporated in vacuo. Purification by flash chromatography (silica, eluent ethyl acetate/n-hexane 1:1, then) affords the product as off-white solid (4.6 g, 88%). MS: m/e=209 (M+H+).

Workup

  1. customfor 12 hours
  2. customThe catalyst is removed by filtration
  3. customthe solution evaporated in vacuo
  4. customPurification by flash chromatography (silica, eluent ethyl acetate/n-hexane 1:1

Sources & evidence

ORD record
ord-56416e7ec0f147a5924106ce38b905ee
Source dataset
uspto-grants-2008_01
Patent number
US07317007B2

Reaction notes

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