Dimethylformamide → 2-Naphthalenecarbonitrile, 6-(phenylmethoxy)-

HRID 1583864Notes

Reaction equation

HRID 1583864 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.N.[CH3:22][N:23](C)C=O>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:22]#[N:23])[CH:15]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6405952-(Benzyloxy)-6-bromonaphthaleneHCID 12896473Azane;hydrate

Product 1

HCID 110864692-Naphthalenecarbonitrile, 6-(phenylmethoxy)-

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

Ten grams of 2-benzyloxy-6-bromonaphthalene was dissolved in 65 ml of dimethyl formamide, 2.83 grams of cuprous cyanide and 5 to 6 drops of pyridine were added thereto, and the mixture was heated to reflux with stirring for twelve hours. After the reaction was completed, the reaction solution was poured into a mixture of 150 ml of concentrated ammonia water and 150 grams of ice, the mixture was extracted with chloroform, the chloroform extract was washed with diluted hydrochloric acid and then with water, dried with anhydrous sodium sulfate, and the solvent was evaporated therefrom. The resulting residue was subjected to a column chromatography using 200 grams of silica gel and eluted with n-hexane and chloroform mixture (1:1) to afford 2-benzyloxy-6-naphthonitrile, colourless crystals, yield 6.8 grams.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. extractionthe mixture was extracted with chloroform
  4. extractionthe chloroform extract
  5. washwas washed with diluted hydrochloric acid
  6. dry with materialwith water, dried with anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. washeluted with n-hexane and chloroform mixture (1:1)

Sources & evidence

ORD record
ord-7862ed1788084972a027a702044a4979
Source dataset
uspto-grants-1985_11
Patent number
US04554275

Reaction notes

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