4-Chlorobenzaldehyde → HCID 20536498, compound

HRID 1389080Notes

Reaction equation

HRID 1389080 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([F:13])[CH:3]=1.[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1>>[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:1][C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([F:13])[CH:3]=2)=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 10797532Ethyl 4-Amino-2-fluorobenzoate

Product 1

HCID 20536498HCID 20536498, compound

Procedure

Ethyl 4-amino-2-fluorobenzoate (17 g), 4-chlorobenzaldehyde (14 g), and 100 ml of absolute alcohol are heated on a steam bath for 10 minutes. Upon cooling, the mixture is filtered. The residue is dried and then dissolved in 200 ml of hot ethanol and 4 g of sodium borohydride is added in portions with stirring. The mixture is then heated under reflux, with stirring, for 3 hours, cooled, added to ice water and filtered to yield ethyl 4-(p-chlorobenzylamino)-2-fluorobenzoate as a solid.

Workup

  1. temperatureUpon cooling
  2. filtrationthe mixture is filtered
  3. customThe residue is dried
  4. dissolutiondissolved in 200 ml of hot ethanol
  5. addition4 g of sodium borohydride is added in portions
  6. temperatureThe mixture is then heated
  7. temperatureunder reflux
  8. stirringwith stirring, for 3 hours
  9. temperaturecooled
  10. additionadded to ice water
  11. filtrationfiltered

Sources & evidence

ORD record
ord-4e4b9d6400e24813bae82775d42737e4
Source dataset
uspto-grants-1981_01
Patent number
US04243609

Reaction notes

Loading…