Potassium Carbonate → 2-Amino-5-ethynyl-6-methylbenzonitrile

HRID 52639Notes

Reaction equation

HRID 52639 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][Si](C)(C)C)=[C:6]([CH3:16])[C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+]>CO>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]#[CH:11])=[C:6]([CH3:16])[C:3]=1[C:4]#[N:5]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 543680762-Amino-5-(trimethylsilylethynyl)-6-methylbenzonitrile

Product 1

HCID 540198812-Amino-5-ethynyl-6-methylbenzonitrileYield 106.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.4 grams (0.006 mole) of 2-amino-5-(trimethylsilylethynyl)-6-methylbenzonitrile and 0.9 gram (0.006 mole) of potassium carbonate in 50 mL of methanol was stirred at ambient temperature for one hour. The reaction mixture was then concentrated under reduced pressure to a residue. The residue was taken up in about 75 mL of water, and the solution was extracted with two 200 mL portions of diethyl ether. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 1.0 gram of 2-amino-5-ethynyl-6-methylbenzonitrile. The NMR spectrum was consistent with the proposed structure. This reaction was repeated several times.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure to a residue
  2. extractionthe solution was extracted with two 200 mL portions of diethyl ether
  3. dry with materialThe combined extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6ca0f8cf077743da931057d9eaae1df2
Source dataset
uspto-grants-1997_04
Patent number
US05616718

Reaction notes

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