2-Chloroquinoline → 4-Chloro-3,8-dimethyl-1-(2-quinolinyl)-1H-pyrazolo[3,4-b]quinoline

HRID 498045

Reaction equation

[CH3:1][C:2]1[C:11]2[N:10]=[C:9]([CH2:12][C:13](=O)[CH3:14])O[C:7](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH:17]([C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1)[NH2:18].[Cl:29]C1C=CC2C(=CC=CC=2)N=1>>[Cl:29][C:1]1[C:2]2[C:11](=[C:6]([CH3:7])[CH:5]=[CH:4][CH:3]=2)[N:10]=[C:9]2[N:17]([C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)[N:18]=[C:13]([CH3:14])[C:12]=12

Participants

Reactant 3

HCID 119282-Chloroquinoline

HCID 851112(1H)-Quinolinone, hydrazone

HCID 223203048-methyl-2-(2-oxopropyl)-4H-3,1-benzoxazin-4-one

Product 1

HCID 223203484-Chloro-3,8-dimethyl-1-(2-quinolinyl)-1H-pyrazolo[3,4-b]quinoline

Procedure

Following the procedure described in Reference Example 2-3 and Example 2-1, the title compound was prepared from 8-methyl-2-(2-oxopropyl)-4H-3,1-benzoxazin-4-one and 2-hydrazinoquinoline which was previously prepared form 2-chloroquinoline following the method described in Reference Example 2-2 (42% yield).

Sources & evidence

ORD record: ord-96aeddbf6a9b4492bdf75d126f24836a
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949648B2

Linked notes

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