Water → 2-amino-4-phenyl-3-furonitrile

HRID 1926867Notes

Reaction equation

HRID 1926867 reaction equation
C(NCC)C.[OH:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O.[C:16](#[N:20])[CH2:17][C:18]#[N:19].O>CN(C=O)C>[NH2:20][C:16]1[O:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:17]=1[C:18]#[N:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8010MalononitrileHCID 8021DiethylamineHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 117898882-amino-4-phenyl-3-furonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add 3.78 ml (36.7 mmol) diethylamine dropwise to a mixture of 10 g (73.4 mmol) hydroxyacetophenone and 4.852 g (73.4 mmol) malononitrile in 24 ml DMF with cooling at RT. Stir the dark mixture for 2 h at RT and then add slowly to water (200 ml), with stirring and cooling. Continue stirring the precipitate for 30 min at approx. 10° C., filter with suction, suspend in water twice more, and filter with suction again. Dry the residue at high vacuum to constant weight. 10.99 g (81.2% of theor.) of the target compound is obtained as a yellowish-brown solid.

Workup

  1. stirringwith stirring
  2. temperaturecooling
  3. stirringContinue stirring the precipitate for 30 min at approx. 10° C.
  4. filtrationfilter with suction
  5. filtrationfilter with suction again
  6. customDry the residue at high vacuum to constant weight
  7. custom10.99 g (81.2% of theor.) of the target compound is obtained as a yellowish-brown solid

Sources & evidence

ORD record
ord-5ac0091be1e048aa87b43910710c5724
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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