Water → HCID 12777809, compound

HRID 2390023Notes

Reaction equation

HRID 2390023 reaction equation
CON(C)[C:4]([CH2:6][C:7]1[N:8]=[CH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=O.[C:18]1([Mg]Br)C=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH2:26]>C1COCC1>[C:6]([C:7]1[N:8]=[CH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:26])[C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 131729961HCID 131729961, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 12777809HCID 12777809, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon gas stream, 168 mg of N-methoxy-N-methylisoquinoline-3-carboxyamide was dissolved in 1 mL of anhydrous THF, followed by stirring under cooling with ice. To the reaction liquid was slowly added 0.8 mL of phenyl magnesium bromide (1 mol/L THF solution), followed by continuously stirring for 30 minutes. Water was added to the reaction liquid, followed by extraction with chloroform. The organic layer was washed with diluted hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue obtained was purified by silica gel chromatography (chloroform alone) to obtain 154 mg (yield 77%) of a title compound as a yellow oily substance.

Workup

  1. temperatureunder cooling with ice
  2. customTo the reaction liquid
  3. stirringby continuously stirring for 30 minutes
  4. extractionfollowed by extraction with chloroform
  5. washThe organic layer was washed with diluted hydrochloric acid and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue obtained
  9. customwas purified by silica gel chromatography (chloroform alone)

Sources & evidence

ORD record
ord-ac6f507ba7934ea3a6b7c75b7ecf6167
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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