Formaldehyde → Ethyl 8-Fluoro-1-((hydroxymethyl)(methyl)amino)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1168535Notes

Reaction equation

C([O:5][C:6]([N:8]([CH3:27])[N:9]1[C:18]2[C:13](=[CH:14][C:15]([I:20])=[CH:16][C:17]=2[F:19])[C:12](=[O:21])[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:10]1)=O)(C)(C)C.C=O>O>[F:19][C:17]1[CH:16]=[C:15]([I:20])[CH:14]=[C:13]2[C:18]=1[N:9]([N:8]([CH2:6][OH:5])[CH3:27])[CH:10]=[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:12]2=[O:21]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of ethyl 1-((tert-butoxycarbonyl)(methyl)amino)-8-fluoro-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (Preparation 35, 0.200 g), 37% aqueous formaldehyde (4.0 mL), and water (2.0 mL) is heated in an oil bath for 2.5 h at 85° C. The mixture is cooled, diluted with ice water (30 mL), and the resulting precipitate is collected, rinsed with ice water and partially air dried. The solid is dissolved in a mixture of acetone and CH2Cl2, dried (Na2SO4), and concentrated at reduced pressure to yield 0.194 g (90%) of the title compound as a white solid. Physical characteristics: MS (ESI+) m/z 421 (M+H)+; TLC (silica gel GF): Rf=0.32 acetone/CH2Cl2 (1/4).

Workup

temperatureThe mixture is cooled
customthe resulting precipitate is collected
washrinsed with ice water and partially air
customdried
dissolutionThe solid is dissolved in a mixture of acetone and CH2Cl2
dry with materialdried (Na2SO4)
concentrationconcentrated at reduced pressure

Sources & evidence

ORD record: ord-91f4aae8d499475c94f0fdaf0046fb96
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06624159B2

Reaction notes

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