Formaldehyde → ethyl 1-[N-(hydroxymethyl)-N-methylamino]-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 1708546Notes

Reaction equation

[CH3:1][NH:2][N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([F:14])[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:4]1.[CH2:22]=[O:23]>O>[OH:23][CH2:22][N:2]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([F:14])[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:4]1)[CH3:1]

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of ethyl 1-methylamino-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (10 g) in water (100 ml) and 37% aqueous formaldehyde (100 ml) was heated to 100° C. for 1 hour. The mixture was cooled and the solid removed by filtration and washed with water. The resulting yellow colored solid was dried to constant weight in vacuo over phosphorus pentaoxide to yield ethyl 1-[N-(hydroxymethyl)-N-methylamino]-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (10.25 g).

Workup

temperatureThe mixture was cooled
customthe solid removed by filtration
washwashed with water
dry with materialThe resulting yellow colored solid was dried to constant weight in vacuo over phosphorus pentaoxide

Sources & evidence

ORD record: ord-6d83cb1adcb3451fb58c64aa70e10f4d
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05359066

Reaction notes

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