Pyridine → N-(7-methoxy-1,8-naphthyridin2-yl)-3-acetoxybenzamide

HRID 580478

Reaction equation

HRID 580478 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[N:5][C:6]([O:12][CH3:13])=[CH:7][CH:8]=2)[N:3]=1.[C:14]([O:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](Cl)=[O:22])(=[O:16])[CH3:15].N1C=CC=CC=1>O>[CH3:13][O:12][C:6]1[N:5]=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([NH:1][C:21](=[O:22])[C:20]3[CH:24]=[CH:25][CH:26]=[C:18]([O:17][C:14](=[O:16])[CH3:15])[CH:19]=3)=[N:3]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 129985583-(Chlorocarbonyl)phenyl acetateHCID 217930277-methoxy-1,8-Naphthyridin-2-amine

Product 1

HCID 13983395N-(7-methoxy-1,8-naphthyridin2-yl)-3-acetoxybenzamideYield 78.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure is similar to that described in Example 3, but starting with 2-amino-7-methoxynaphthyridine (3.5 g), 3-acetoxybenzoyl chloride (4.4 g) and anhydrous pyridine (40 cc). The reaction mixture is poured into water (400 cc) and the precipitate obtained is separated by filtration and then washed with water (6×100 cc) and dried in the air. On recrystallization from ethanol (140 cc) of the product thereby obtained, N-(7-methoxy-1,8-naphthyridin2-yl)-3-acetoxybenzamide (5.3 g), m.p. 172° C., is obtained.

Workup

  1. customthe precipitate obtained
  2. customis separated by filtration
  3. washwashed with water (6×100 cc)
  4. customdried in the air
  5. customOn recrystallization from ethanol (140 cc) of the product
  6. customthereby obtained

Sources & evidence

ORD record
ord-2e02604d1e1447bfb7a6e3d9f54c6d2c
Source dataset
uspto-grants-1988_06
Patent number
US04753941

Linked notes

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