Acetic Acid → HCID 12083049, compound

HRID 1168522Notes

Reaction equation

HRID 1168522 reaction equation
[H-].[Na+].[C:3]([O:6][CH2:7][C:8]1[CH:9]=[C:10]([CH3:24])[CH:11]=[C:12]2[C:17]=1[N:16]=[CH:15][C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:13]2[OH:23])(=[O:5])[CH3:4].Cl[C:26]([O:28][CH2:29][CH:30]([CH3:32])[CH3:31])=[O:27].C(O)(=O)C>CN1CCCC1=O.C(OCC)(=O)C>[C:3]([O:6][CH2:7][C:8]1[CH:9]=[C:10]([CH3:24])[CH:11]=[C:12]2[C:17]=1[N:16]([C:26]([O:28][CH2:29][CH:30]([CH3:32])[CH3:31])=[O:27])[CH:15]=[C:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]2=[O:23])(=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 62365Isobutyl chloroformateHCID 178469637HCID 178469637, compound

Product 1

HCID 12083049HCID 12083049, compoundYield 49.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Sodium hydride (3.1 g, 60% dispersion) is added at 0° C. to a stirred solution of ethyl 8-((acetyloxy)methyl)-4-hydroxy-6-methyl-3-quinolinecarboxylate (Preparation 25, 29.6 g) in N-methylpyrrolidinone (250 ml). The solution is allowed to warm to room temperature over 10 min and isobutyl chloroformate (25.5 g) is then added. After 30 min, acetic acid (3.6 g) is added. The solvent is evaporated under reduced pressure, and the residual oil is partitioned between ethyl acetate and water. The ethyl acetate layer is concentrated to give an oil. The crude product is dissolved in ethyl acetate (50 ml) and is chromatographed on silica gel with 10% ethyl acetate/hexane as the initial eluant to give 19.5 g of the title compound. A sample is recrystallized from ethyl acetate/hexane for analysis. Physical characteristics: M.p. 101-103° C.; 1H NMR (CDCl3) δ1.05, 1.44, 2.12, 2.18, 2.59, 4.15, 4.45, 5.82, 7.74, 7.88, 9.40. Anal. Found: C, 62.42; H, 6.34; N, 3.45.

Workup

  1. customThe solvent is evaporated under reduced pressure
  2. customthe residual oil is partitioned between ethyl acetate and water
  3. concentrationThe ethyl acetate layer is concentrated
  4. customto give an oil
  5. customis chromatographed on silica gel with 10% ethyl acetate/hexane as the initial eluant

Sources & evidence

ORD record
ord-47b1fa68c2234c5b8124ea5ff6decacd
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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