Water → 2-(6-Methoxynaphthalen-2-yl)propanenitrile

HRID 372926

Reaction equation

HRID 372926 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:17])[C:14]([NH2:16])=O)[CH:7]=[CH:6]2.FC(F)(F)C(OC(=O)C(F)(F)F)=O.O>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([CH3:17])[C:14]#[N:16])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 962WaterHCID 9845Trifluoroacetic anhydrideHCID 6040272-(6-Methoxy-2-naphthyl)propanamide

Product 1

HCID 6073442-(6-Methoxynaphthalen-2-yl)propanenitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 50 ml of dry THF, were suspended 3.0 g of oa (6-methoxy-2-naphthyl)-propanamide, followed by adding thereto 8.3 g of trifluoroacetic anhydride and then stirring at room temperature for 12 hours. The resulting reaction mixture was poured into 200 ml of iced water, and then precipitated white solid was filtered off. After purifying with silica gel column, the product was recrystallized twice with ethanol to obtain 2.1 g of oa (6-methoxy-2-naphthyl)propanonitrile (Compound No. 1-1) of this invention.

Workup

  1. additionby adding
  2. customThe resulting reaction mixture
  3. customprecipitated white solid
  4. filtrationwas filtered off
  5. customAfter purifying with silica gel column
  6. customthe product was recrystallized twice with ethanol

Sources & evidence

ORD record
ord-36aa1caa17354845b23a00117b375c0a
Source dataset
uspto-grants-1992_11
Patent number
US05160662

Linked notes

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