Methyl vinyl ketone → HCID 12781344, compound

HRID 1863118Notes

Reaction equation

HRID 1863118 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]2[O:11][CH2:12][O:13][C:4]=2[CH:3]=1.[CH:14]([C:16]([CH3:18])=O)=[CH2:15]>>[CH2:12]1[O:11][C:5]2[C:4](=[C:3]3[C:2](=[C:7]([N+:8]([O-:10])=[O:9])[CH:6]=2)[N:1]=[CH:15][CH:14]=[C:16]3[CH3:18])[O:13]1

Participants

3

Reactant 2

HCID 6570Methyl vinyl ketoneHCID 6026656-Nitro-1,3-benzodioxol-5-amine

Product 1

HCID 12781344HCID 12781344, compoundYield 63%

Procedure

4-Amino-1,2-methylenedioxy-5-nitrobenzene was made according to the method of Lott, et al.--J. Amer. Chem. Soc., 70, 3621 (1848). It was subjected to a Skraup reaction with methyl vinyl ketone to provide 5,6-methylenedioxy-4-methyl-8-nitroquinoline. The crude compound was crystallized from acetone to give a 63% yield of pure substance; mp 183°-185°.

Sources & evidence

ORD record
ord-191439ce78e84f8e987a3245e31466e5
Source dataset
uspto-grants-1979_09
Patent number
US04167638

Reaction notes

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