Water → 2-methyl-4-nitro-N-(7-chloro-1,8-naphthyridin-2-yl)-benzamide

HRID 328279Notes

Reaction equation

HRID 328279 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[N:18][C:19]([Cl:25])=[CH:20][CH:21]=2)[N:16]=1.O>N1C=CC=CC=1>[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[N:18][C:19]([Cl:25])=[CH:20][CH:21]=2)[N:16]=1)=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 851997-Chloro-1,8-naphthyridin-2-amineHCID 128464852-Methyl-4-nitrobenzoyl chloride

Product 1

HCID 214443672-methyl-4-nitro-N-(7-chloro-1,8-naphthyridin-2-yl)-benzamideYield 94%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Methyl-4-nitro-benzoyl chloride (16.1 g.) is added all at once to a suspension of 2-amino-7-chloro-1,8-naphthyridine (14.5 g.) in pyridine (161 cc.). The temperature rises to 40° C. The mixture is stirred for a further hour and water (640 cc.) is then added. The precipitate is filtered off and washed with water (225 cc.) and then with acetone (150 cc.). After recrystallisation from acetonitrile (1,600 cc.), 2-methyl-4-nitro-N-(7-chloro-1,8-naphthyridin-2-yl)-benzamide (26 g.) melting at 229° C is obtained.

Workup

  1. customrises to 40° C
  2. filtrationThe precipitate is filtered off
  3. washwashed with water (225 cc.)
  4. customAfter recrystallisation from acetonitrile (1,600 cc.)

Sources & evidence

ORD record
ord-011e71be5ca243c48f335eb02e4e66bc
Source dataset
uspto-grants-1977_04
Patent number
US04016274

Reaction notes

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