3,5-Dichloroaniline → 2-(3,5-Dichlorophenylamino)nicotinic acid

HRID 2227796Notes

Reaction equation

HRID 2227796 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[NH2:15]>C(O)(=O)C>[Cl:11][C:12]1[CH:13]=[C:14]([NH:15][C:2]2[N:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH:16]=[C:17]([Cl:19])[CH:18]=1

Participants

4

Reactant 2

HCID 122813,5-DichloroanilineHCID 762582-Chloronicotinic acid

Product 1

HCID 126276192-(3,5-Dichlorophenylamino)nicotinic acidYield 97.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Chloronicotinic acid (10 g) was combined with 3,5-dichloroaniline (15 g) in 150 mL acetic acid and heated at reflux for 4 hr. Upon cooling, a white solid formed which was collected by filtration, washed with acetic acid, water, and dried to give 17.6 g of 2-(3,5-dichlorophenylamino)nicotinic acid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hr
  3. temperatureUpon cooling
  4. customa white solid formed which
  5. filtrationwas collected by filtration
  6. washwashed with acetic acid, water
  7. customdried

Sources & evidence

ORD record
ord-49906059e42f44d1a88a703f71e97cdc
Source dataset
uspto-grants-2002_07
Patent number
US06414153B1

Reaction notes

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