Dichloromethane → 5-Acetyl-2,3-dimethoxybenzonitrile

HRID 2254774Notes

Reaction equation

HRID 2254774 reaction equation
N[C:2]1[C:3]([O:13][CH3:14])=[C:4]([O:11][CH3:12])[CH:5]=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[Cu][C:16]#[N:17].[C-]#N.[K+].C(Cl)Cl>O.Cl>[C:16]([C:2]1[C:3]([O:13][CH3:14])=[C:4]([O:11][CH3:12])[CH:5]=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1)#[N:17]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 9032Potassium CyanideHCID 214591851-(3-Amino-4,5-dimethoxyphenyl)ethanoneHCID 178418546HCID 178418546, compound

Product 1

HCID 214589805-Acetyl-2,3-dimethoxybenzonitrile

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 5.2 g of sodium nitrile in 20 ml of water is added dropwise at 0° within 20 minutes to 14.0 g of 5'-amino-3',4'-dimethoxyacetophenone dissolved in 155 ml of 1N hydrochloric acid. After stirring at -2° for 30 minutes the cold diazonium salt solution is added dropwise within 30 minutes at 5°-10° to a solution of 8.7 g of copper(I) cyanide and 5.45 g of potassium cyanide in 60 ml of water. After completion of the addition 200 ml of methylene chloride are added, and the reaction mixture is stirred at 23° for 3 hours and then filtered. The organic phase is separated, washed with water, dried over sodium sulfate and evaporated. The residue is recrystallized from methylene chloride/petroleum ether. There is obtained 5'-cyano-3',4'-dimethoxyacetophenone of m.p. 125°-126°.

Workup

  1. additionare added
  2. filtrationfiltered
  3. customThe organic phase is separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue is recrystallized from methylene chloride/petroleum ether

Sources & evidence

ORD record
ord-2d544767598344e5934acce3ca8f700f
Source dataset
uspto-grants-1993_08
Patent number
US05236952

Reaction notes

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