Dimethylformamide → HCID 46224429, compound

HRID 1474528Notes

Reaction equation

HRID 1474528 reaction equation
[CH3:1][N:2]([CH:4]=O)[CH3:3].[O:6]1[CH:10]=[CH:9][C:8]([C:11]2[C:20](=[O:21])[C:19]3[C:18]4[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=4[CH:16]=[C:15]([O:26][CH2:27][CH2:28][CH3:29])C=3NC=2)=[CH:7]1.[H-].[Na+].CI>C(OCC)(=O)C.O>[O:6]1[CH:10]=[CH:9][C:8]([C:11]2[C:20](=[O:21])[C:19]3[C:18]4[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=4[CH:16]=[C:15]([O:26][CH2:27][CH2:28][CH3:29])[C:3]=3[N:2]([CH3:1])[CH:4]=2)=[CH:7]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 46224398HCID 46224398, compound

Product 1

HCID 46224429HCID 46224429, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a DMF solution (5 ml) of 2-furan-3-yl-5-propoxy-4H-benzo[f]quinolin-1-one (300 mg, 0.94 mmol) was added sodium hydride (60% oil base, 61 mg, 1.4 mmol), and then the mixture was stirred at room temperature for 5 minutes. Methyl iodide (181 mg, 1.27 mmol) was added thereto and the resulting mixture was stirred at room temperature for 62 hours. Water and ethyl acetate were added to the reaction mixture and the resulting mixture was subjected to separation. The thus-obtained organic layer was washed with water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:ethyl acetate=90:1→80:1). The purified product was concentrated under reduced pressure to recrystallize the residue from ethyl acetate-n-hexane, giving a pale gray powder of 2-furan-3-yl-4-methyl-5-propoxy-4H-benzo[f]quinolin-1-one (130 mg, yield: 42%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 62 hours
  2. customthe resulting mixture was subjected to separation
  3. washThe thus-obtained organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified
  7. concentrationThe purified product was concentrated under reduced pressure
  8. customto recrystallize the residue from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-0d922e83f2fd41c6bb3a9aac10edc3f0
Source dataset
uspto-grants-2015_04
Patent number
US09018229B2

Reaction notes

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