HCID 59394970, compound → HCID 59395040, compound

HRID 383425Notes

Reaction equation

HRID 383425 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-])=O)=[C:6]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:7]=1>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:16])=[C:6]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:7]=1

Participants

4

Reactant 1

HCID 59394970HCID 59394970, compound

Product 1

HCID 59395040HCID 59395040, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

4-[2-(5-Methyl-2-nitro-phenyl)ethyl]morpholine (150 mg, 0.599 mmol) and Pd (10%, wet) (128 mg, 0.0599 mmol) were brought up in methanol (5 mL) under H2 atmosphere and stirred vigorously for 1 h at 40° C. The reaction was filtered and concentrated in vacuo to provide 4-methyl-2-(2-morpholinoethyl)aniline (110 mg, 0.499 mmol, 83%) as an amber oil. LC/MS m/z 221.2 [M+H]+. 1H NMR (400.0 MHz, DMSO-d6) δ 6.72-6.68 (m, 2H), 6.51 (d, J=7.9 Hz, 1H), 4.64 (s, 2H), 3.58 (t, J=4.6 Hz, 4H), 2.57-2.53 (m, 2H), 2.44-2.40 (m, 6H), 2.11 (s, 3H).

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d81f077fa9b4562a5e043a6e089749d
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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