Veratric Acid → HCID 13983398, compound

HRID 580481Notes

Reaction equation

HRID 580481 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.[NH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[N:18][C:19]([Cl:25])=[CH:20][CH:21]=2)[N:16]=1>>[Cl:25][C:19]1[N:18]=[C:17]2[C:22]([CH:23]=[CH:24][C:15]([NH:14][C:6](=[O:8])[C:5]3[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=3)=[N:16]2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 7121Veratric AcidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13983398HCID 13983398, compoundYield 49.9%

Procedure

The procedure is similar to that described in Example 2, but starting with 3,4-dimethoxybenzoic acid (14.6 g), N,N'-carbonyldiimidazole (12.9 g) and 2-amino-7-chloro-1,8-naphthyridine (8.9 g), and heating for 17 hours under reflux. The product obtained, after precipitation of the reaction mixture in water (1000 cc) and drying, is purified by recrystallization in acetonitrile (250 cc). N-(7-Chloro-1,8-naphthyridin-2-yl)-3,4-dimethoxybenzamide (8.5 g), m.p. 196° C., is thereby obtained.

Workup

  1. temperatureheating for 17 hours
  2. temperatureunder reflux
  3. customThe product obtained
  4. customafter precipitation of the reaction mixture in water (1000 cc)
  5. customdrying
  6. customis purified by recrystallization in acetonitrile (250 cc)

Sources & evidence

ORD record
ord-c0869881cba1402a9cd8680d66cbf2fc
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Reaction notes

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