4-Chloro-6,7-dimethoxyquinazoline → 4-(6-Chloro-5-nitro-2,3-dihydro-indol-1-yl)-6,7-dimethoxy-quinazoline

HRID 1597955Notes

Reaction equation

HRID 1597955 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][NH:8]2)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].Cl[C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][N:16]=1>CN1CCCC1=O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[CH:17][N:16]=2)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 189329026-chloro-5-nitro-2,3-dihydro-1H-indole

Product 1

HCID 189327424-(6-Chloro-5-nitro-2,3-dihydro-indol-1-yl)-6,7-dimethoxy-quinazolineYield 24%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Utilizing a procedure analogous to that described in Example 47 this product was prepared in 24% yield from 6-chloro-5-nitro-indoline (1.1 eq.), and 4-chloro-6,7-dimethoxy-quinazoline (1.0 eq) in N-methyl-pyrrolidinone. (M.P. 276°-278° C.; LC-MS: 387 (MH+); anal. RP18-HPLC RT: 4.48 min.).

Sources & evidence

ORD record
ord-b766cbcd1e4242f0a17841214724231a
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

Loading…