Veratrylamine → 4-(3,4-Dimethoxyphenylmethylamino)-6,7-diethoxy-3-quinolinecarbonitrile

HRID 1934942Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[CH2:25][NH2:26]>>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:25][NH:26][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:15][CH2:16][CH3:17])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:18]#[N:19])[CH:27]=[CH:28][C:29]=1[O:30][CH3:31]

Participants

Reactant 2

HCID 79832Veratrylamine

HCID 107788724-Chloro-6,7-diethoxyquinoline-3-carbonitrile

Product 1

HCID 102014434-(3,4-Dimethoxyphenylmethylamino)-6,7-diethoxy-3-quinolinecarbonitrile

Procedure

In the manner of Example 61 reaction of 4-chloro-6,7-diethoxy-3-quinolinecarbonitrile with 3,4-dimethoxybenzylamine gave the title compound as a tan solid, mp 200-204° C.

Sources & evidence

ORD record: ord-3710a5d8acb845e89a29eb8e5f377650
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384051B1

Reaction notes

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