Triethylamine → 5-(2-Methylmorpholino)-2-nitroaniline

HRID 1047569Notes

Reaction equation

HRID 1047569 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[CH3:12][CH:13]1[O:18][CH2:17][CH2:16][NH:15][CH2:14]1.C(N(CC)CC)C>CN1C(=O)CCC1>[CH3:12][CH:13]1[CH2:14][N:15]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=2)[NH2:7])[CH2:16][CH2:17][O:18]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 742185-Chloro-2-nitroanilineHCID 4106152-Methylmorpholine

Product 1

HCID 683849655-(2-Methylmorpholino)-2-nitroanilineYield 70%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

5-Chloro-2-nitroaniline (200 mg, 1.159 mmol) was added to a solution of 2-methylmorpholine (176 mg, 1.738 mmol) in NMP (5 mL) in the presence of triethylamine (0.404 mL, 2.90 mmol). The reaction mixture was heated via microwave irradiation to 100° C. for 1 h. and upon cooling, the solvent was removed by vacuum. Purification by flash column chromatography (5% CH3OH/CH2Cl2) afforded the title compound as a solid in a 70% yield. 1H NMR: (400 MHz, DMSO-d6): δ 7.79 (d, 1H, J=9.6 Hz), 7.25 (bs, 2H), 6.39 (dd, 1H, J=2.8 and 9.6 Hz), 6.20 (d, 1H, J=2.8 Hz), 3.88 (dd, 1H, J=2.8 and 12.0 Hz), 3.69 (d, 1H, J=12.8 Hz), 3.56 (m, 2H), 2.82 (m, 1H), 2.15 (t, 1H, J=7.6 Hz), 1.88 (m, 1H), 1.12 (d, 3H, J=6.0 Hz).

Workup

  1. temperatureupon cooling
  2. customthe solvent was removed by vacuum
  3. customPurification by flash column chromatography (5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-946c785a1ea945dd812bc0ca35e4a921
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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