Ethanol → 4-Methoxy-3-morpholin-4-yl-phenylamine

HRID 1262027Notes

Reaction equation

HRID 1262027 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(O)C.[H][H]>[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 702EthanolHCID 223531674-(2-Methoxy-5-nitrophenyl)morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 176047884-Methoxy-3-morpholin-4-yl-phenylamineYield 87.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-(2-Methoxy-5-nitro-phenyl)-morpholine (0.600 g, 2.52 mmol) was dissolved in Ethanol (35.0 mL, 599 mmol) and the solution was carefully poured over 10% Palladium on Carbon (0.300 g, 22.5 mmol) under nitrogen. The mixture was then placed on a Parr hydrogenation apparatus and was allowed to shake at 55 psi until uptake of hydrogen ceased. The catalyst was then filtered to afford 460 mg of 4-Methoxy-3-morpholin-4-yl-phenylamine without further purification. (M+H)=209.2. 1H NMR (400 MHz, DMSO, d6) δ 6.62 (d, 1H, J=8.36 Hz), 6.15 (m, 1H), 6.13 (m, 1H), 4.56 (s, 2H), 3.69 (m, 4H), 3.65 (s, 3H), 2.89 (m, 4H).

Workup

  1. filtrationThe catalyst was then filtered

Sources & evidence

ORD record
ord-e38e93fda8434613a1f9066d23c68093
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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