Nitric Acid → 5-Chloro-6-methoxy-4-methyl-8-nitroquinolin-2(1H)-one

HRID 1018030Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([Cl:15])=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH:7]=[C:6]2[CH3:14].[N+:16]([O-])([OH:18])=[O:17].O>S(=O)(=O)(O)O>[N+:16]([C:11]1[CH:12]=[C:3]([O:2][CH3:1])[C:4]([Cl:15])=[C:5]2[C:10]=1[NH:9][C:8](=[O:13])[CH:7]=[C:6]2[CH3:14])([O-:18])=[O:17]

Participants

Conditions

Temperature: 0 °C

Procedure

In a 200 ml, three-necked round bottom flask equipped with a mechanical stirrer, thermowatch, and addition funnel was placed 96% sulfuric acid (50 ml) and 6-methoxy-5-chloro-4-methyl-2-quinolone (10) (12.0 g, 53.66 mmoles). This was cooled to 0° C., then a solution of 70% nitric acid(6.04 g, 67.1 mmoles) in 96% sulfuric acid (10 ml) was added dropwise over 35 minutes. The mixture was stirred for 90 minutes at 0° C., then poured into 350 ml of water. The crude orange-brown solid was collected by suction filtration, washed with water (three×20 ml) and air dried. Crude yield is 10.82 g.

Workup

customIn a 200 ml, three-necked round bottom flask equipped with a mechanical stirrer
additionthermowatch, and addition funnel
filtrationThe crude orange-brown solid was collected by suction filtration
washwashed with water (three×20 ml) and air
customdried

Sources & evidence

ORD record: ord-558b700b77334e71b39a7f880569c2a8
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479660B1

Reaction notes

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