1-Iodo-2,3,4-trimethoxybenzene → HCID 10449991, compound

HRID 1453983Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](I)=[C:5]([O:10][CH3:11])[C:4]=1[O:12][CH3:13].C([Li])CCC.[CH3:19][N:20]([CH3:32])[C:21]1[CH:30]=[C:29]2[C:24]([C:25](=O)[CH2:26][CH2:27][O:28]2)=[CH:23][CH:22]=1>>[CH3:19][N:20]([CH3:32])[C:21]1[CH:30]=[C:29]2[C:24]([C:25]([C:7]3[CH:8]=[C:3]([O:2][CH3:1])[C:4]([O:12][CH3:13])=[C:5]([O:10][CH3:11])[CH:6]=3)=[CH:26][CH2:27][O:28]2)=[CH:23][CH:22]=1

Participants

Reactant 3

HCID 2569311-Iodo-2,3,4-trimethoxybenzene

HCID 20312680HCID 20312680, compound

HCID 178418339Butyllithium

Product 1

HCID 10449991HCID 10449991, compound

Procedure

Compounds of this invention having the Formulae I-IV can also be prepared as illustrated by examplary reactions in Scheme V. A phenyl propionitrile is prepared from the condensation of acrylonitrile and dimethylaminophenol. The nitrile was hydrolysed to the acid and the intermediate compound cyclized to yield 7-dimethylamino-chroman-4-one. Trimethoxyiodobenzene was lithiated with butyl lithium and treated with 7-dimethylamino-chroman-4-one to produce dimethyl-[4-(3,4,5-trimethoxy-phenyl)-2H-chromen-7-yl]-amine. Alternatively, 7-dimethylamino-chroman-4-one could be first treated with copper chloride, followed by the addition of lithio trimethoxybenzene, to produce [3-chloro-4-(3,4,5-trimethoxy-phenyl)-2H-chromen-7-yl]-dimethyl-amine.

Sources & evidence

ORD record: ord-ae66b99f8070402a9d1992592ebaf31e
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07476741B2

Reaction notes

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