m,alpha-Dichlorotoluene → 1-(3-Chloro-benzyl)-3-(2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one

HRID 227144Notes

Reaction equation

HRID 227144 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][CH:14]=3)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[Cl:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]Cl)[CH:26]=1>>[Cl:24][C:25]1[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=1)[CH2:31][N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22](=[O:23])[C:13]([C:11]([C:9]2[CH:8]=[CH:7][C:6]3[O:1][CH2:2][CH2:3][O:4][C:5]=3[CH:10]=2)=[O:12])=[CH:14]1

Participants

3

Reactant 2

HCID 12103m,alpha-DichlorotolueneHCID 577545433-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one

Product 1

HCID 577545341-(3-Chloro-benzyl)-3-(2,3-dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-oneYield 24.4%

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1, from 3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one 70 mg (0.228 mmol) and 71.1 mg (0.296 mmol) 1-Chloro-3-chloromethyl-benzene, to give 24 mg of desired compound. LCMS (M+H)+: 432.

Sources & evidence

ORD record
ord-79795f5e90bc4702b8153e640d843ab0
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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