Nicotinic Acid → HCID 13579411, compound

HRID 235848Notes

Reaction equation

HRID 235848 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=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>C(#N)C>[Cl:21][C:15]1[N:14]=[C:13]2[C:18]([CH:19]=[CH:20][C:11]([NH:10][C:1]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)=[O:9])=[N:12]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 938Nicotinic AcidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13579411HCID 13579411, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with nicotinic acid (3.7 g), N,N'-carbonyldiimidazole (4.9 g) and 2-amino-7-chloro-1,8-naphthyridine (3.6 g). The product precipitated in the mixture is separated by filtration, washed with tetrahydrofuran (3×20 cc) and water (3×50 cc), and is then dried at 50° C. under reduced pressure (0.067 kPa). The product produced (4.75 g; m.p. 200° C.) is dissolved in boiling acetonitrile (435 cc). After 2 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with acetonitrile (3×20 cc) and dried at 50° C. under reduced pressure (0.067 kPa). N-(7-chloro-1,8-naphthyridin-2-yl)-3-pyridylcarboxamide (3.9 g) is produced, m.p. 200° C.

Workup

  1. customThe product precipitated in the mixture
  2. customis separated by filtration
  3. washwashed with tetrahydrofuran (3×20 cc) and water (3×50 cc)
  4. customis then dried at 50° C. under reduced pressure (0.067 kPa)
  5. customThe product produced (4.75 g; m.p. 200° C.)
  6. dissolutionis dissolved
  7. customthe crystallised solid is separated by filtration
  8. washwashed with acetonitrile (3×20 cc)
  9. customdried at 50° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-dd8143829c064e9782b13aca71bcecdb
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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