Isopropanol → HCID 13579405, compound

HRID 235813Notes

Reaction equation

HRID 235813 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[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.CC(O)C>O>[Cl:22][C:16]1[N:15]=[C:14]2[C:19]([CH:20]=[CH:21][C:12]([NH:11][C:6](=[O:8])[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)=[N:13]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 99734-Fluorobenzoic AcidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13579405HCID 13579405, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with 4-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 (14.3 g; m.p. 230° C.) is dissolved in boiling 2-propanol (800 cc). After 4 hours' cooling at 4° C., the crystallised solid is separated by filtration, washed with 2-propanol (3×10 cc) and dried at 40° C. under reduced pressure (0.067 kPa). N-(7-chloro-1,8-naphthyridin-2-yl)-4-fluorobenzamide (10.3 g) is produced, m.p. 236° C. EXAMPLE 16

Workup

  1. dissolutionis dissolved
  2. customthe crystallised solid is separated by filtration
  3. washwashed with 2-propanol (3×10 cc)
  4. customdried at 40° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-55f3da94cadc48f1b5189d2ad19e0b4c
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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