Hydrochloric Acid → HCID 25059694, compound

HRID 2244074Notes

Reaction equation

HRID 2244074 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[C:5](C#N)=[CH:4][N:3]=1.C[Mg+].[Br-].CC[O:20][CH2:21][CH3:22].Cl.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[C:5]([C:21](=[O:20])[CH3:22])=[CH:4][N:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 25059693HCID 25059693, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 25059694HCID 25059694, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the solution of 1-amino-6-fluoro-isoquinoline-4-carbonitrile (3 g, 1 eq) in toluene (100 mL) is added 3M MeMgBr in ether (53 mL, 10 eq) at 0° C., then the mixture is stirred at RT for 2 h, then refluxed overnight. The reaction is cooled down and acidified by 2 N HCl aq. to pH˜3, then neutralized by Sat'd NaHCO3 aq (300 mL), extracted by dichloromethane (3×150 mL). The organic layer is dried over Na2SO4, filtered, concentrated to give product 1-(1-amino-6-fluoro-isoquinolin-4-yl)-ethanone (0.8 g, 24%). LC/MS m/z=205 [M+H]+.

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction is cooled down
  3. extractionextracted by dichloromethane (3×150 mL)
  4. dry with materialThe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f3e576355bd54c5ba2b311aa5cc510b9
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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