1-Propanol → HCID 13579403, compound

HRID 235811Notes

Reaction equation

HRID 235811 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[N:13]=1.C(O)CC>O>[Cl:22][C:16]1[N:15]=[C:14]2[C:19]([CH:20]=[CH:21][C:12]([NH:11][C:4](=[O:6])[C:3]3[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=3[F:1])=[N:13]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 10311-PropanolHCID 99352-Fluorobenzoic acidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13579403HCID 13579403, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with 2-fluorobenzoic acid (11.2 g), N,N'-carbonyldiimidazole (12.9 g) and 2-amino-7-chloro-1,8-naphthyridine (8.9 g). The product produced by precipitation in water (13.6 g; m.p. 218° C.) is dissolved in boiling 1-propanol (450 cc). After 3 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with 1-propanol (3×20 cc) and dried at 40° C. under reduced pressure (0.067 kPa). N-(7-chloro-1,8-naphthyridin-2-yl)-2-fluorobenzamide (8.3 g) is produced, m.p. 222° C. EXAMPLE 14

Workup

  1. dissolutionis dissolved
  2. customthe crystallised solid is separated by filtration
  3. washwashed with 1-propanol (3×20 cc)
  4. customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-4e10c67e1e494e3d8851cead836e9c0e
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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