Sodium Cyanide → HCID 178510361, compound

HRID 1791954Notes

Reaction equation

HRID 1791954 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[N:4][CH:3]=1.[Cu](C#N)[C:14]#[N:15].[C-]#N.[Na+]>>[C:14]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[N:4][CH:3]=1)#[N:15]

Participants

4

Reactant 3

HCID 8929Sodium CyanideHCID 3197724-Bromo-1-hydroxyisoquinolineHCID 178418260HCID 178418260, compound

Product 1

HCID 178510361HCID 178510361, compoundYield 52.3%

Conditions

Temperature
180 °C

Procedure

4-Bromo-1-hydroxyisoquinoline (1.56 g) was dissolved in N-methyl-2-pyrrolidine (25 mL), and copper cyanide (1.56 g) was added thereto. The mixture was stirred at 180° C. for 4 hr with heating. The reaction mixture was added to cool to 100° C. and added to an aqueous solution (125 mL) of sodium cyanide (31.25 g). The mixture was extracted with dichloromethane and the extract was dried and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 4-cyano-1-hydroxyisoquinoline (0.62 g) as a pale-yellow solid.

Workup

  1. temperaturewith heating
  2. additionThe reaction mixture was added
  3. temperatureto cool to 100° C.
  4. extractionThe mixture was extracted with dichloromethane
  5. customthe extract was dried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e297209212a341e9b02c2b927f4d1f4b
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

Loading…