Hydrochloric Acid → 1,4-Dihydro-3-hydroxymethyl-5-methyl-8-nitro-4-oxoquinoline

HRID 613564Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[C:4](=[O:15])[CH:5]=[CH:6][NH:7]2.[O:16]1COCO[CH2:17]1.Cl>O1CCOCC1>[OH:16][CH2:17][C:5]1[C:4](=[O:15])[C:3]2[C:8](=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][C:2]=2[CH3:1])[NH:7][CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred mixture of 1,4-dihydro-5-methyl-8-nitro-4-oxoquinoline (1.5 g) and 1,3,5-trioxane (3.31 g) in dioxane (15 ml) was added conc. hydrochloric acid (30 ml), and the mixture was stirred at 100° C. overnight. The mixture was evaporated in vacuo, and the residue was treated with acetonitrile to give 1,4-dihydro-3-hydroxymethyl-5-methyl-8-nitro-4-oxoquinoline (1.3 g).

Workup

customThe mixture was evaporated in vacuo
additionthe residue was treated with acetonitrile

Sources & evidence

ORD record: ord-3043f2e64ca143c4b1cbb15485cb5a33
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06008230

Reaction notes

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