Sodium Cyanide → HCID 11644805, compound

HRID 418833Notes

Reaction equation

HRID 418833 reaction equation
Br[CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.[C-:21]#[N:22].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.CO>[OH:20][C:17]1[CH:18]=[CH:19][C:14]([C:4]2[O:5][C:6]3[C:11]([C:12](=[O:13])[C:3]=2[CH2:2][C:21]#[N:22])=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:15][CH:16]=1

Participants

7

Reactant 3

HCID 8929Sodium CyanideHCID 11430Potassium CarbonateHCID 66650305HCID 66650305, compound

Product 1

HCID 11644805HCID 11644805, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-bromomethyl-2-(4-hydroxyphenyl)-4H-chromen-4-one (0.3 g, 0.8 mmol) in DMF (15 mL), water (15 mL), and NaCN (0.12 g, 2.4 mmol) was stirred at 45° C. for 24 h. The reaction mixture was extracted with EtOAc (3×100 mL) and concentrated to afford a solid residue. This residue was re-dissolved in MeOH (50 mL) and water (50 mL) and was mixed with potassium carbonate (1 g) and stirred at rt for 0.5 h. MeOH was removed, the aqueous layer was acidified with HCl (1 N) to pH=5. The solid was filtered off and then purified by column chromatography (hexane:EtOAc 1:2). The resulting solid was re-crystallized from dichloromethane and hexanes to give 2-(2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl)acetonitrile as a light yellow solid product (0.14 g, 63%). MS (ES) m/z: 278.94 (M+1), 277.93 (M); Mp. 258.2-259.5° C.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc (3×100 mL)
  2. concentrationconcentrated
  3. customto afford a solid residue
  4. customMeOH was removed
  5. filtrationThe solid was filtered off
  6. custompurified by column chromatography (hexane:EtOAc 1:2)
  7. customThe resulting solid was re-crystallized from dichloromethane and hexanes

Sources & evidence

ORD record
ord-a2b298fa53814edaa32b888ceb82d303
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

Loading…