Morpholine → 2-Morpholino-5-nitrobenzonitrile

HRID 1825643Notes

Reaction equation

HRID 1825643 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-4d669daf9fac467baf4629f3539f9451
Source dataset
uspto-grants-2006_05
Patent number
US07045514B2

Reaction notes

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