Water → Ethyl 8-Fluoro-6-iodo-1-(methylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1168534Notes

Reaction equation

HRID 1168534 reaction equation
FC(F)(F)C(O)=O.C(O[C:13]([N:15](C)[N:16]1[C:25]2[C:20](=[CH:21][C:22]([I:27])=[CH:23][C:24]=2[F:26])[C:19](=[O:28])[C:18]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:17]1)=O)(C)(C)C.C(=O)(O)[O-].[Na+].O>C(Cl)Cl>[F:26][C:24]1[CH:23]=[C:22]([I:27])[CH:21]=[C:20]2[C:25]=1[N:16]([NH:15][CH3:13])[CH:17]=[C:18]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:19]2=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 12083058Ethyl 1-((tert-Butoxycarbonyl)(methyl)amino)-8-fluoro-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate

Product 1

HCID 12083059Ethyl 8-Fluoro-6-iodo-1-(methylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of trifluroacetic acid (6.40 g) in methylene chloride (5 mL) is added dropwise over a 4 minute period to a solution of ethyl 1-((tert-butoxycarbonyl)(methyl)amino)-8-fluoro-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (Preparation 34, 1.10 g) in methylene chloride (20 mL) at room temperature. After 3.5 h, the mixture is poured into a mixture of saturated sodium bicarbonate solution (125 mL) and water (50 mL), and extracted two times with ethyl acetate. The combined organic extracts are dried (Na2SO4) and concentrated at reduced pressure. The resulting gummy solid is stirred with diethyl ether at room temperature to afford 0.857 g (98%) of the title compound as a white solid.

Workup

  1. extractionextracted two times with ethyl acetate
  2. dry with materialThe combined organic extracts are dried (Na2SO4)
  3. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-6962e63c3a1646fda836dbffdede0ffd
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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