Dimethylformamide → HCID 22243547, compound

HRID 890951Notes

Reaction equation

HRID 890951 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[C:10]([O:17][CH3:18])[CH:11]=[CH:12][CH:13]=2)[CH:8]=1)(=O)=O.[CH3:21][N:22](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:18][O:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[CH:8]=[C:7]([C:21]#[N:22])[CH:16]=[CH:15]2

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 22243572HCID 22243572, compound

Product 1

HCID 22243547HCID 22243547, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A solution of 8-methoxy-2-naphthyl trifluoromethanesulfonate (871 mg, 2.8 mmol) in DMF (4 mL) is degassed by repeatedly evacuating the flask then flushing with N2. Zinc cyanide (200 mg, 1.7 mmol) is added followed by Pd(PPh3)4 (165 mg, 0.14 mmol). The resulting mixture is again degassed and heated to 80° C. for 3 hours. The reaction is allowed to cool, poured into water and washed four times with ether. The combined organic extracts are dried (Na2SO4), filtered, and concentrated. The resulting material is purified by column chromatography (step gradient, 10–30% CH2Cl2 in hexanes) to give 8-methoxy-2-naphthonitrile as a white solid (493, 84%). HRMS (EI) calculated for C12H9NO: 183.0684, found 183.0681.

Workup

  1. customby repeatedly evacuating the flask
  2. customthen flushing with N2
  3. customThe resulting mixture is again degassed
  4. temperatureto cool
  5. additionpoured into water
  6. washwashed four times with ether
  7. dry with materialThe combined organic extracts are dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting material is purified by column chromatography (step gradient, 10–30% CH2Cl2 in hexanes)

Sources & evidence

ORD record
ord-2b2ea4cec4b64872a7f29f9eab7f733d
Source dataset
uspto-grants-2006_02
Patent number
US07001900B2

Reaction notes

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