1,1'-Carbonyldiimidazole → 5,6-Dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HRID 719800Notes

Reaction equation

HRID 719800 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[NH2:23])[CH2:16][CH2:15][CH2:14]1>O1CCCC1>[NH:23]1[C:21]2=[C:22]3[C:17](=[CH:18][CH:19]=[CH:20]2)[CH2:16][CH2:15][CH2:14][N:13]3[C:1]1=[O:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 1046728-Quinolinamine, 1,2,3,4-tetrahydro-

Product 1

HCID 156467025,6-Dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 1,1′-carbonyldiimidazole in tetrahydrofuran was added to a solution of 1,2,3,4-tetrahydro-8-quinolineamine (10 g) obtained in Reference Example 130 in tetrahydrofuran (100 ml), and the mixture was stirred at room temperature at 4 hours. The reaction mixture was concentrated to give a brown solid (11 g). Further recrystallization from water-ethyl estate afforded the title compound as colorless crystals (10 g).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-55ba1929ff91454a90ce525a64f99240
Source dataset
uspto-grants-2006_11
Patent number
US07132547B2

Reaction notes

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