Hydrochloric Acid → HCID 86732727, compound

HRID 525861Notes

Reaction equation

HRID 525861 reaction equation
[OH:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]([O:15]CC)=[O:14])[CH:9]=2)[N:4]([CH3:18])[CH:3]=1.[H-].[Na+].Cl[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1.[OH-].[Li+].Cl>CN(C)C=O.O.CO>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][O:1][C:2]2[C:11](=[O:12])[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:13]([OH:15])=[O:14])[CH:9]=3)[N:4]([CH3:18])[CH:3]=2)=[CH:24][CH:25]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 86732726HCID 86732726, compound

Product 1

HCID 86732727HCID 86732727, compoundYield 67.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a suspension of ethyl 3-hydroxy-1-methyl-4-oxo-1,4-dihydroquinoline-6-carboxylate (6.7 g, 27.1 mmol) in N,N-dimethylformamide (18.0 ml) at 0° C. was added sodium hydride (2.168 g, 54.2 mmol), and the mixture was stirred for 20 min. At this time, 1-(chloromethyl)-4-methoxybenzene (3.7 ml, 27.3 mmol) was added and the reaction was heated to 75° C. and allowed to stir for 2 h. After cooling, the reaction was poured into ice, and the resulting precipitate was filtered, washed with water and diethyl ether, collected, and dried. Methanol (24.00 ml), water (8.00 ml) and lithium hydroxide (0.86 g, 35.9 mmol) were added, and the reaction was stirred at 60° C. for 2 h. The reaction was cooled and the pH was adjusted to 3-4 by addition of 2N hydrochloric acid (18.00 ml, 36 mmol). The resulting precipitate was filtered, washed with water and diethyl ether, and dried to give 3-((4-methoxybenzyl)oxy)-1-methyl-4-oxo-1,4-dihydroquinoline-6-carboxylic acid (6.1937 g, 18.25 mmol, 67.4% yield. LCMS: (M+H)+: 340.1.

Workup

  1. stirringto stir for 2 h
  2. temperatureAfter cooling
  3. additionthe reaction was poured into ice
  4. filtrationthe resulting precipitate was filtered
  5. washwashed with water and diethyl ether
  6. customcollected
  7. customdried
  8. stirringthe reaction was stirred at 60° C. for 2 h
  9. temperatureThe reaction was cooled
  10. filtrationThe resulting precipitate was filtered
  11. washwashed with water and diethyl ether
  12. customdried

Sources & evidence

ORD record
ord-a6bd8149b5f849a5b569579b5fc813af
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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