Potassium Carbonate → HCID 86732763, compound

HRID 525900Notes

Reaction equation

HRID 525900 reaction equation
[Cl:1][C:2]1[C:11]([OH:12])=[C:10]([OH:13])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:19])[C:5]([C:16]([OH:18])=[O:17])=[CH:6][N:7]2[CH2:14][CH3:15].[C:20]([O-:23])([O-])=O.[K+].[K+].Cl[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1>CN(C)C=O>[Cl:1][C:2]1[C:11]([O:12][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[C:10]([O:13][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:19])[C:5]([C:16]([O:18][CH2:4][C:3]1[CH:8]=[CH:9][C:10]([O:23][CH3:20])=[CH:11][CH:2]=1)=[O:17])=[CH:6][N:7]2[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 12873132HCID 12873132, compound

Product 1

HCID 86732763HCID 86732763, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a red suspension of 5-chloro-1-ethyl-6,7-dihydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (12.2 g, 43.0 mmol), K2CO3 (23.78 g, 172 mmol) and KI (0.714 g, 4.30 mmol) in N,N-Dimethylformamide (DMF) (200 mL) at r.t. was added 1-(chloromethyl)-4-methoxybenzene (19.26 mL, 142 mmol). The mixture was heated at 90° C. for 4 h. After cooling, the mixture was concentrated and partitioned between water (200 mL) and DCM (200 mL), and extracted with DCM (150 mL) twice. The organic layers were combined, dried and concentrated. The crude product was purified twice through column chromatography eluting with EtOAc/hexanes (0-100%) to afford pure 4-methoxybenzyl 5-chloro-1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylate (14 g, 20.65 mmol, 48.0% yield) as a white solid. LCMS: (M+H)+: 644.1.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. custompartitioned between water (200 mL) and DCM (200 mL)
  4. extractionextracted with DCM (150 mL) twice
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was purified twice through column chromatography
  8. washeluting with EtOAc/hexanes (0-100%)

Sources & evidence

ORD record
ord-1a02b387b5054031880be1013ab0b546
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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