Ethanol → HCID 13787387, compound

HRID 2413924Notes

Reaction equation

HRID 2413924 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([OH:7])=O.[NH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[N:16][C:17]([Cl:23])=[CH:18][CH:19]=2)[N:14]=1.C(O)C>O>[Cl:23][C:17]1[N:16]=[C:15]2[C:20]([CH:21]=[CH:22][C:13]([NH:12][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([Cl:11])=[C:2]([Cl:1])[CH:3]=3)=[N:14]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 58173,4-Dichlorobenzoic acidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13787387HCID 13787387, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is analogous to that described in Example 1, but starting with 3,4-dichlorobenzoic acid (15.3 g), N,N'-carbonyldiimidazole (12.9 g) and 2-amino-7-chloro-1,8-naphthyridine (8.9 g). The product obtained by precipitation in water (17.6 g; m.p. 228° C.) is dissolved in boiling ethanol (900 cc). After cooling for 2 hours at 4° C., the crystallized solid is separated by filtration, washed with isopropyl ether (2×30 cc) and dried at 40° C. under reduced pressure (0.07 kPa). N-(7-Chloro-1,8-naphthyridin-2-yl)-3,4-dichlorobenzamide (9.2 g), m.p. 230° C., is obtained.

Workup

  1. dissolutionis dissolved
  2. customthe crystallized solid is separated by filtration
  3. washwashed with isopropyl ether (2×30 cc)
  4. customdried at 40° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-a88e4cca355d4184a467ec9a3d7629ab
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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