Ethyl 2-methylacetoacetate → HCID 67606900, compound

HRID 1613926Notes

Reaction equation

HRID 1613926 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][CH:9]([C:15]([CH3:17])=O)[C:10]([O:12]CC)=[O:11]>>[NH:1](/[C:15](/[CH3:17])=[C:9](/[CH3:8])\[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 701Ethyl 2-methylacetoacetateHCID 6115Aniline

Product 1

HCID 67606900HCID 67606900, compound

Procedure

In the process of the invention, the 3-methyl substituted compound among the starting 2-formyl-3-substituted-4-(hydroxy or acyloxy) quinoline derivatives represented by the general formula (II) can be prepared by subjecting aniline to dehydration condensation with ethyl 2-methylacetoacetate to form a 3-anilino-2-methylcrotonic acid derivative, followed by intramolecular cyclization by heating to high temperature of, preferably, 200° to 250° C. to obtain 2, 3-dimethyl-4-quinoline. Moreover, this compound may further reacted with an anhydrous alkanoic acid such as, for example, acetic anhydride, to obtain 2, 3-dimethyl-4-acyloxyquinoline, e.g. 2, 3-dimethyl-4-acetoxyquinoline, followed by oxidation with selenium dioxide in an aqueous organic solvent to obtain the derivative.

Workup

  1. customcan be prepared

Sources & evidence

ORD record
ord-448c3ec50b4548f78a694300b65d43a0
Source dataset
uspto-grants-1993_03
Patent number
US05194617

Reaction notes

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