Arsenic Acid → 4-Methyl-5,6-dimethoxy-8-nitroquinoline

HRID 1388558Notes

Reaction equation

HRID 1388558 reaction equation
[CH3:1][O:2][C:3]1[C:9]([O:10][CH3:11])=[CH:8][C:6]([NH2:7])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[CH:15]([C:17]([CH3:19])=O)=[CH2:16].P(=O)(O)(O)O.[As](=O)(O)(O)O>>[CH3:11][O:10][C:9]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]2[C:8]=1[C:17]([CH3:19])=[CH:15][CH:16]=[N:7]2

Participants

5

Reactant 4

HCID 234Arsenic AcidHCID 1004Phosphoric AcidHCID 6570Methyl vinyl ketoneHCID 46531524,5-Dimethoxy-2-nitroaniline

Product 1

HCID 6191084-Methyl-5,6-dimethoxy-8-nitroquinolineYield 30%

Procedure

Compound II was treated with commercially-available methyl vinyl ketone in the presence of phosphoric acid and arsenic acid to afford the intermediate 5,6-dimethoxy-4-methyl-8-nitroquinoline (III), a new compound, as a pure crystalline material in 30% yield. This successful reaction is novel in that the steric hindrance provided by the 2-methoxy group of 4-amino-5-nitroveratrole and by the methyl group of methyl vinyl ketone would be expected by those skilled in the art to prevent the ring-closure reaction to form III from occurring.

Sources & evidence

ORD record
ord-44c2ca7d571148a5ae260a73b2f0b1d4
Source dataset
uspto-grants-1984_02
Patent number
US04431807

Reaction notes

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