Water → 6-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-1-isoindolinone

HRID 328282Notes

Reaction equation

HRID 328282 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([NH:12][C:13](=[O:24])[C:14]3[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=3[CH:21](Cl)Cl)=[N:9]2)=[CH:4][CH:3]=1.[OH2:25]>CN(C)C=O.[N+]([O-])([O-])=O.[Ag+]>[Cl:20][C:18]1[CH:19]=[C:14]2[C:15]([CH:21]([OH:25])[N:12]([C:8]3[CH:7]=[CH:6][C:5]4[C:10](=[N:11][C:2]([Cl:1])=[CH:3][CH:4]=4)[N:9]=3)[C:13]2=[O:24])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 962Water2×HCID 214443647-Chloro-2-(5-chloro-2-dichloromethyl-benzoylamino)-1,8-naphthyridine

Product 1

HCID 198422416-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-1-isoindolinone

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of silver nitrate (12.1 g.) in water (50 cc.) is added to a solution of 7-chloro-2-(5-chloro-2-dichloromethyl-benzoylamino)-1,8-naphthyridine (9.5 g.) in dimethylformamide (300 cc.) heated to a temperature of about 110° C. The reaction mixture is further heated to a temperature of about 110° C for 20 minutes and the suspension obtained is filtered hot. The filtrate obtained is poured into water (500 cc.) and the product which precipitates is filtered off. Recrystallisation from dimethylformamide gives 6-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-1-isoindolinone (5 g.) melting at 306° C.

Workup

  1. temperatureThe reaction mixture is further heated to a temperature of about 110° C for 20 minutes
  2. customthe suspension obtained
  3. filtrationis filtered hot
  4. customThe filtrate obtained
  5. customthe product which precipitates
  6. filtrationis filtered off
  7. customRecrystallisation from dimethylformamide

Sources & evidence

ORD record
ord-6fc3b039a82541ec92d621eecd59d5c5
Source dataset
uspto-grants-1977_04
Patent number
US04016274

Reaction notes

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