Hexane → (E)-2-(4-fluoro-1-indanylidene)-acetamide

HRID 1954878Notes

Reaction equation

HRID 1954878 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5]/[C:6]/2=[CH:11]\[C:12](Cl)=[O:13].[OH-].[NH4+:16].CCCCCC>ClCCl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5]/[C:6]/2=[CH:11]\[C:12]([NH2:16])=[O:13]

Participants

5

Reactant 3

HCID 8058HexaneHCID 14923Ammonium HydroxideHCID 23293683(E)-2-(4-fluoro-1-indanylidene)acetyl Chloride

Product 1

HCID 11137943(E)-2-(4-fluoro-1-indanylidene)-acetamideYield 58.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice cold solution of (E)-2-(4-fluoro-1-indanylidene)acetyl chloride (2.11 g, 0.01 mol) in dichloromethane (65 mL) was treated with a 30% aqueous solution of ammonium hydroxide (2.63 ml, 0.02 mol), and the mixture was stirred for 18 h. Hexane was added to the mixture, and the solids were collected by filtration to give 1.63 g of crude product. Recrystallization from acetonitrile:water mixtures gave 1.11 g (58%) of (E)-2-(4-fluoro-1-indanylidene)-acetamide as a white solid; m.p., 198-200° C.

Workup

  1. filtrationthe solids were collected by filtration
  2. customto give 1.63 g of crude product
  3. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-2cfcf630c262476f886702965a8a33a6
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

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