Morpholine → 2-Morpholino-5-nitrobenzonitrile

HRID 2414494Notes

Reaction equation

HRID 2414494 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][C:8]=1F)#[N:2].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[N:13]1([C:8]2[CH:7]=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=2[C:1]#[N:2])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 5194172-Fluoro-5-nitrobenzonitrile

Product 1

HCID 74104812-Morpholino-5-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

3-Cyano-4-fluoronitrobenzene (3.3 g, 19.9 mmol) was dissolved in ethyl acetate (10 mL). Morpholine (2.2 mL, 25 mmol), and N,N-diisopropylethylamine (3.5 mL, 20 mmol) were added and the mixture stirred overnight at room temperature. At 17 h, additional ethyl acetate (150 mL) was added and the combined mixture was washed with water (50 mL) and brine (50 mL), dried (Na2SO4), filtered and concentrated under vacuum. The residue was used without further purification.

Workup

  1. waitAt 17 h
  2. washthe combined mixture was washed with water (50 mL) and brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was used without further purification

Sources & evidence

ORD record
ord-2a690e23eb4647b9b46f35bafcb2639c
Source dataset
uspto-grants-2004_11
Patent number
US06812225B2

Reaction notes

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