4-Fluoroaniline → HCID 21450978, compound

HRID 596184Notes

Reaction equation

HRID 596184 reaction equation
[Cl:1][C:2]1[C:3]([O:5][C:6](=[O:9])[C:7]=1[Cl:8])=[O:4].[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>C1C=CC=CC=1>[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:6](=[O:9])/[C:7](/[Cl:8])=[C:2](/[Cl:1])\[C:3]([OH:5])=[O:4])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 70728Dichloromaleic anhydride

Product 1

HCID 21450978HCID 21450978, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

8.35g (0.05 mol) of 2,3-dichloromaleic anhydride was dissolved in 50 ml of benzene. To the resulting solution 20 ml of benzene solution containing 5.55g (0.05 mol) of 4-fluoroaniline was added dropwise over a period of 20 min. at temperatures of 5°-10° C under agitation. After completing the addtion, the mixture was agitated at 5°-10° C for 30 min. to form crystals, which were separated by filtration and washed with benzene to obtain 13.15g of N-(4-fluorophenyl)-2,3-dichloromaleamic acid in the form of white crystal melting at 222°-225° C (yield, 95%). The results of elementary analysis were as follows:

Workup

  1. additionwas added dropwise over a period of 20 min. at temperatures of 5°-10° C under agitation
  2. customto form crystals, which
  3. customwere separated by filtration
  4. washwashed with benzene

Sources & evidence

ORD record
ord-57c4bd1d7cbe436bb792a6871f12049e
Source dataset
uspto-grants-1977_03
Patent number
US04010182

Reaction notes

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