Morpholine → 5-Morpholino-2-nitroaniline

HRID 1047557Notes

Reaction equation

HRID 1047557 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].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(N(CC)CC)C>CN1C(=O)CCC1>[O:15]1[CH2:16][CH2:17][N:12]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=2)[NH2:7])[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 5967255-Morpholino-2-nitroanilineYield 77%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5-chloro-2-nitroaniline (100 mg, 0.58 mmol) in NMP (4.5 mL) was treated with morpholine (75 mg, 0.86 mmol) in the presence of triethylamine (0.2 mL, 1.44 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 afforded the title compound in a 77% yield. 1H NMR: (400 MHz, DMSO-d6): δ 7.82 (d, 1H, J=9.6 Hz), 7.29 (bs, 2H), 6.39 (dd, 1H, J=2.8 and 9.6 Hz), 6.22 (d, 1H, J=2.4 Hz), 3.70 (m, 4H), 3.27 (m, 4H).

Workup

  1. temperatureupon cooling
  2. customthe solvent was removed by vacuum
  3. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-47578f7052f549278ff13a02344ed8bb
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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