Sodium Cyanide → HCID 84660451, compound

HRID 639914Notes

Reaction equation

HRID 639914 reaction equation
C([N:4]1[C:13]([C:14]#[N:15])=[C:12](C2C=CC=C(F)C=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:23]C)[CH:10]=2)[C:5]1=[O:25])C=C.[C-]#N.[Na+]>CS(C)=O.[OH-].[Na+].C(Cl)Cl>[OH:23][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5](=[O:25])[NH:4][C:13]([C:14]#[N:15])=[CH:12]2

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 11739125HCID 11739125, compound

Product 1

HCID 84660451HCID 84660451, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-allyl-4-(3-fluorophenyl)-6-methoxy-1-oxo-1,2-dihydroisoquinoline-3-carbonitrile (2.0 g) in 24 mL DMSO was added NaCN (1.47 g). The reaction was heated to 150 C for 6.5 h, then diluted with 1N NaOH and extracted with EtOAc (2×). The organic solutions were extracted once with 1N NaOH. The combine aqueous solutions were acidified with conc. HCl and extracted with EtOAc (3×). All organic solutions were combined and dried (MgSO4), then concentrated to give a dark solid. The solid was suspended in CH2Cl2 and filtered to give 1.04 g of 2-allyl-4-3-fluorophenyl)-6-hydroxy-1-oxo-1,2-dihydroisoquinoline-3-carbonitrile, which was used without further purification.

Workup

  1. temperatureThe reaction was heated to 150 C for 6.5 h
  2. extractionextracted with EtOAc (2×)
  3. extractionThe organic solutions were extracted once with 1N NaOH
  4. extractionextracted with EtOAc (3×)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give a dark solid
  8. filtrationfiltered

Sources & evidence

ORD record
ord-b3c00dc4690143afb0a3f900a5193a08
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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