3-Chlorobenzoic Acid → HCID 20154394, compound

HRID 2413918Notes

Reaction equation

HRID 2413918 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[NH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:17][CH:18]=2)[N:13]=1.C(#N)C>O>[C:22]1([C:16]2[N:15]=[C:14]3[C:19]([CH:20]=[CH:21][C:12]([NH:11][C:5](=[O:7])[C:4]4[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=4)=[N:13]3)=[CH:18][CH:17]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 6342AcetonitrileHCID 13787372HCID 13787372, compound

Product 1

HCID 20154394HCID 20154394, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is analogous to that described in Example 1, but starting with 3-chlorobenzoic acid (1.6 g), N,N'-carbonyldiimidazole (1.6 g) and 2-amino-7-phenyl-1,8-naphthyridine (1.6 g). The product obtained by precipitation in water (2.2 g; m.p. approximately 160° C.) is dissolved in boiling acetonitrile (200 cc). After cooling for 4 hours at 4° C., the crystallized solid is separated by filtration, washed with acetonitrile (3×10 cc) and dried at 40° C. under reduced pressure (0.07 kPa). N-(7-Phenyl-1,8-naphthyridin-2-yl)-3-chlorobenzamide (1.5 g), m.p. 175° C., is obtained.

Workup

  1. dissolutionis dissolved
  2. customthe crystallized solid is separated by filtration
  3. washwashed with acetonitrile (3×10 cc)
  4. customdried at 40° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-01b8b6956e294e5e87957f598f5f9824
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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