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

HRID 502665Notes

Reaction equation

HRID 502665 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[C:11](#[N:15])[CH2:12][C:13]#[N:14].C(N(CC)CC)C>CO>[NH2:15][C:11]1[O:1][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:12]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 8471TriethylamineHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 117898882-amino-4-phenyl-3-furonitrileYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of hydroxyacetophenone (10 g, 73.2 mmol) in methanol (200 mL) was added malononitrile (4.85 g, 73.4 mmol). Triethylamine (10.23 mL, 73.3 mmol) was then added slowly. The resulting dark solution was stirred overnight at room temperature. The mixture was then evaporated onto silica and purified by flash column chromatography (20% acetone/hexane) to afford the product as a pale yellow solid (6.6 g, 49%).

Workup

  1. customThe mixture was then evaporated onto silica
  2. custompurified by flash column chromatography (20% acetone/hexane)

Sources & evidence

ORD record
ord-450939abba494bdca7413eaaad08eae8
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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