Morpholine → 2-Morpholin-4-yl-5-nitrophenol

HRID 929686Notes

Reaction equation

HRID 929686 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[OH:17].C(N(CC)CC)C>CN1C(=O)CCC1>[O:4]1[CH2:5][CH2:6][N:1]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2[OH:17])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 128671362-Bromo-5-nitrophenol

Product 1

HCID 230715652-Morpholin-4-yl-5-nitrophenol

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

Morpholine (59.9 mg, 0.688 mmol) was added to a solution of 2-bromo-5-nitrophenol (100 mg, 0.459 mmol) and triethylamine (0.070 ml, 0.505 mmol) in NMP. The reaction mixture was heated via microwave irradiation to 200° C. for 1 h. The reaction was monitored by TLC. After completion of the reaction and following cooling, the solvent was removed in vacuo and the resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2) to provide the title compound as a solid. 1H NMR: (CDCl3, 400 MHz): δ 7.82-7.79 (m, 2H), 7.20 (m, 1H), 6.69 (bs, 1H), 3.89 (m, 4H), 2.95 (m, 4H). ESI-MS: 225.1 [M+H]+.

Workup

  1. customAfter completion of the reaction
  2. temperaturefollowing cooling
  3. customthe solvent was removed in vacuo
  4. customthe resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-d3c0331f51b243af80593319db5fa2c5
Source dataset
uspto-grants-2016_03
Patent number
US09296703B2

Reaction notes

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