2-Chlorobenzoic Acid → HCID 13983392, compound

HRID 580477Notes

Reaction equation

HRID 580477 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[N:13]=1>O1CCCC1>[Cl:22][C:16]1[N:15]=[C:14]2[C:19]([CH:20]=[CH:21][C:12]([NH:11][C:4](=[O:6])[C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=3[Cl:1])=[N:13]2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 83742-Chlorobenzoic AcidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13983392HCID 13983392, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

N,N'-Carbonyldiimidazole (12.9 g) is added to a solution of 2-chlorobenzoic acid (12.5 g) in anhydrous tetrahydrofuran (250 cc). The mixture is stirred for 2 hours at a temperature in the region of 20° C., until the evolution of gas has ceased. 2-Amino-7-chloro-1,8-naphthyridine (8.9 g) is then added and the mixture is heated under reflux for 22 hours. The reaction mixture is poured into distilled water (2000 cc), and the precipitate formed is separated by filtration, washed with water and dried in the air. On recrystallization from ethanol (180 cc) of the product thereby obtained, N-(7-chloro-1,8-naphthyridin-2-yl)-2-chlorobenzamide (6.9 g), m.p. 180° C., is obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 22 hours
  3. additionThe reaction mixture is poured
  4. distillationinto distilled water (2000 cc)
  5. customthe precipitate formed
  6. customis separated by filtration
  7. washwashed with water
  8. customdried in the air
  9. customOn recrystallization from ethanol (180 cc) of the product
  10. customthereby obtained

Sources & evidence

ORD record
ord-774fd55458944847bfa4cb61111a8737
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Reaction notes

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