Diethyl Ether → HCID 15096200, compound

HRID 359136Notes

Reaction equation

HRID 359136 reaction equation
C([Li])CCC.C(OCC)C.Br[C:12]1[CH:13]=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2.CN(OC)[C:24](=[O:28])[CH2:25][CH2:26][CH3:27]>C1COCC1>[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[C:12]([C:24](=[O:28])[CH2:25][CH2:26][CH3:27])[CH:13]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 214133-BromoquinolineHCID 13704543N-Methoxy-N-methylbutyramideHCID 178418339Butyllithium

Product 1

HCID 15096200HCID 15096200, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a dry 3-necked flask under argon at -50° C., n-butyl lithium (0.0025 M, 0.021 ml) was added to 150 ml diethylether. Then 4.16 grams 3-bromoquinoline in 2 ml THF was added dropwise while stirring and maintaining the temperature at -60° C. to -55° C. The solution was stirred for 30 minutes, and 2.3 grams N-methyl-N-methoxybutanamide were then added dropwise at -50° C. and the solution was stirred an additional 30 minutes The solution was then allowed to warm to 0° C. and stirred for one hour. The reaction was quenched with a saturated solution of ammonium chloride and the THF layer separated, washed with brine, separated, and dried over magnesium sulfate. Filtration through diatomaceous earth, followed by concentration and subsequent thin layer chromatography (35% ethylacetate/65% CH2Cl2) gave a total yield of 2.03 g (51%) of the title compound.

Workup

  1. temperaturemaintaining the temperature at -60° C. to -55° C
  2. stirringThe solution was stirred for 30 minutes
  3. stirringthe solution was stirred an additional 30 minutes The solution
  4. stirringstirred for one hour
  5. customThe reaction was quenched with a saturated solution of ammonium chloride
  6. customthe THF layer separated
  7. washwashed with brine
  8. customseparated
  9. dry with materialdried over magnesium sulfate
  10. filtrationFiltration through diatomaceous earth
  11. concentrationfollowed by concentration and subsequent thin layer chromatography (35% ethylacetate/65% CH2Cl2)

Sources & evidence

ORD record
ord-7ea8a76bb9914ee8a6dae306dd9e5ae9
Source dataset
uspto-grants-1991_03
Patent number
US04999431

Reaction notes

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