Ammonium Hydroxide → (E)-2-(6-fluoro-1-indanylidene)acetamide

HRID 1954860Notes

Reaction equation

HRID 1954860 reaction equation
[OH-].[NH4+:2].[F:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9]/[C:10]/2=[CH:13]\[C:14](Cl)=[O:15])=[CH:6][CH:5]=1>ClCCl>[F:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9]/[C:10]/2=[CH:13]\[C:14]([NH2:2])=[O:15])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 15491026(E)-2-(6-fluoro-1-indanylidene)acetyl chloride

Product 1

HCID 9837001(E)-2-(6-fluoro-1-indanylidene)acetamideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 29.6% aqueous ammonium hydroxide solution (17.6 mL, 134 mmol) was added dropwise to a stirred, chilled (ice bath) solution of (E)-2-(6-fluoro-1-indanylidene)acetyl chloride (14.1 g, 67 mmol) in dichloromethane (165 mL). After an hour, the resulting white precipitate was collected by filtration, dissolved in ethyl acetate (600 mL) and washed with water (3×300 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated in vacuo. The resulting off-white solid was washed with hexane, giving 11.6 g (91%) of (E)-2-(6-fluoro-1-indanylidene)acetamide, m.p., 180-183° C.;

Workup

  1. waitAfter an hour
  2. filtrationthe resulting white precipitate was collected by filtration
  3. dissolutiondissolved in ethyl acetate (600 mL)
  4. washwashed with water (3×300 mL)
  5. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. washThe resulting off-white solid was washed with hexane

Sources & evidence

ORD record
ord-8c3726e4dd34455da5cece7591b6c72e
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

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