Isonicotinic Acid → HCID 13983401, compound

HRID 580482Notes

Reaction equation

HRID 580482 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][CH:2]=1.[NH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[N:14][C:15]([Cl:21])=[CH:16][CH:17]=2)[N:12]=1>>[Cl:21][C:15]1[N:14]=[C:13]2[C:18]([CH:19]=[CH:20][C:11]([NH:10][C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)=[O:9])=[N:12]2)=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 5922Isonicotinic AcidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13983401HCID 13983401, compoundYield 36.4%

Procedure

The procedure is similar to that described in Example 2, but starting with 4-pyridinecarboxylic acid (6.2 g), N,N'-carbonyldiimidazole (8.1 g) and 2-amino-7-chloro-1,8-naphthyridine (9 g). The product obtained, after precipitation in water (500 cc), washing with tetrahydrofuran (50 cc), then washing with water (200 cc) and drying (9.8 g; m.p. approximately 220° C.), is purified by crystallization in acetonitrile (850 cc). N-(7-Chloro-1,8-naphthyridin-2-yl)-4-pyridinecarboxamide (5.2 g), m.p. 228° C., is thereby obtained.

Workup

  1. customThe product obtained
  2. customafter precipitation in water (500 cc)
  3. washwashing with tetrahydrofuran (50 cc)
  4. washwashing with water (200 cc)
  5. customdrying (9.8 g; m.p. approximately 220° C.)
  6. customis purified by crystallization in acetonitrile (850 cc)

Sources & evidence

ORD record
ord-ab544d8dbdee42a4934e7e7706101a32
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Reaction notes

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