Morpholine → Morpholino(3-nitrophenyl)methanone

HRID 1487144Notes

Reaction equation

HRID 1487144 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C(Cl)Cl.CN(C=O)C>[O:29]1[CH2:30][CH2:31][N:26]([C:7]([C:6]2[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:9])[CH2:27][CH2:28]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 84973-Nitrobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 225453Morpholino(3-nitrophenyl)methanoneYield 69.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To stirred solution of 3-nitrobenzoic acid (5 g, 29.9 mmol) in DCM: DMF (30 ml, 29:1) was added oxalyl chloride (3.14 ml, 35.9 mmol) dropwise at RT. Resulting reaction mixture was stirred for 1 h. The mixture was concentrated and the residue was dissolved in DCM (25 ml), the reaction mixture was cooled to 0° C. and triethylamine (6.26 ml, 44.9 mmol) and morpholine (3.13 ml, 35.9 mmol) were added and the reaction mixture was stirred for 1 h. The reaction mixture was concentrated under vacuum and the residue was diluted with cold water, the solid separated out was filtered and washed with n-hexanes and dried under vacuum to give the product (4.9 g).

Workup

  1. customResulting
  2. customreaction mixture
  3. concentrationThe mixture was concentrated
  4. dissolutionthe residue was dissolved in DCM (25 ml)
  5. stirringthe reaction mixture was stirred for 1 h
  6. concentrationThe reaction mixture was concentrated under vacuum
  7. additionthe residue was diluted with cold water
  8. customthe solid separated out
  9. filtrationwas filtered
  10. washwashed with n-hexanes
  11. customdried under vacuum

Sources & evidence

ORD record
ord-2ceddaf9a6db4f9eb02bae758ec6561c
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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