4-Fluoroaniline → HCID 54567662, compound

HRID 377136Notes

Reaction equation

HRID 377136 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12]([C:14]#[C:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:13])[CH3:10]>>[CH2:19]([O:18][C:16]([CH:15]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:14][C:12]([O:11][CH2:9][CH3:10])=[O:13])=[O:17])[CH3:20]

Participants

3

Reactant 2

HCID 97314-FluoroanilineHCID 69803Diethyl acetylenedicarboxylate

Product 1

HCID 54567662HCID 54567662, compound

Procedure

A solution of 10.0 g (0.09 mole) 4-fluoroaniline 7 and 8.0 g (0.047 mole) diethylacetylene dicarboxylate 8 is stirred at room temperature for 72 hours. The crude product is purified by flash chromatography using silica gel eluted initially with ethyl acetate:hexane (1:4) and finally with ethyl acetate. The fractions containing the product are combined and concentrated under reduced pressure to give 9 as a yellow oil.

Workup

  1. customThe crude product is purified by flash chromatography
  2. washeluted initially with ethyl acetate:hexane (1:4) and finally with ethyl acetate
  3. additionThe fractions containing the product
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f073c4b7e26b44fe89a2d8d65c7d98f3
Source dataset
uspto-grants-2000_02
Patent number
US06024937

Reaction notes

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