Water → HCID 68446011, compound

HRID 502939Notes

Reaction equation

HRID 502939 reaction equation
[C:1]([C:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[F:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28]Br)=[CH:24][CH:23]=1.O>CN(C=O)C>[F:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13](=[O:14])[C:4]([C:1](=[O:3])[CH3:2])=[CH:5]2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 2450413-Acetylquinolin-4(1H)-one

Product 1

HCID 68446011HCID 68446011, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-acetyl-4(1H)-quinolinone (1a) (0.8 g, 45 mmol) in dry DMF (40 mL) was treated with anhydrous K2CO3 (0.86 g, 62 mmol) and 4-fluorophenylmethylbromide (2.46 g, 13 mmol) and the resulting suspension was stirred for 1.5 hours at 100° C. After cooling, water was added (100 mL) and the precipitate that formed was filtered, washed with water, light petroleum ether in turn and then dried under IR lamp to provided compound 2a (0.86 g, 65%); mp 213-214° C. (toluene). Analogs 2b (R1═C1, R2═H) and 2c (R1═H, R2═Cl) were similarly prepared by this method. Compound 2b: 92% yield; mp 214-216° C. (toluene/cyclohexane); compound 2c: 73% yield; mp 185-187° C. (toluene/cyclohexane).

Workup

  1. temperatureAfter cooling
  2. customthe precipitate that formed
  3. filtrationwas filtered
  4. washwashed with water, light petroleum ether in turn
  5. customdried under IR lamp

Sources & evidence

ORD record
ord-a67cb562089d4ac4b2212a0c9be62932
Source dataset
uspto-grants-2010_08
Patent number
US07776883B2

Reaction notes

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