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Pyridine → 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-diethylaminocarbonyloxy-isoindolin-1-one

HRID 66337
Notes
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Reaction equation

HRID 66337 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([OH:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])=[N:9]2)=[CH:4][CH:3]=1.[CH2:23]([N:25]([CH2:29][CH3:30])[C:26](Cl)=[O:27])[CH3:24].C(N(CC)CC)C.N1C=CC=CC=1>C(Cl)Cl.O>[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([O:21][C:26]([N:25]([CH2:29][CH3:30])[CH2:23][CH3:24])=[O:27])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])=[N:9]2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1049PyridineHCID 6916Diethylcarbamoyl chlorideHCID 8471TriethylamineHCID 199004082-(7-Chloro-1,8-naphthyridin-2-yl)-3-hydroxyisoindolin-1-one

Product 1

HCID 227547412-(7-Chloro-1,8-naphthyridin-2-yl)-3-diethylaminocarbonyloxy-isoindolin-1-oneYield 57.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

The procedure of Example 21 is followed but starting with 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-isoindolin-1-one (6.2 g.) in methylene chloride (300 cc.), diethylcarbamoyl chloride (8.15 g.), triethylamine (8.4 cc.) and pyridine (30 cc.). Water (250 cc.) is added to the reaction mixture after it has been stirred for 48 hours at a temperature of about 20° C. The precipitate formed is filtered off and recrystallised from diisopropyl ether (800 cc.) to give 2-(7-chloro-1,8-naphthyridin-2-yl)-3-diethylaminocarbonyloxy-isoindolin-1-one (4.7 g.) melting at 142°-144° C.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. customrecrystallised from diisopropyl ether (800 cc.)

Sources & evidence

ORD record
ord-5c9a789c3a32422c83bb9b1833d78db1
Source dataset
uspto-grants-1978_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04131674

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes