Water → 7-Aminocarbonyl-6-chloro-2,3-dihydro-2,2-dimethylbenzofuran

HRID 52648Notes

Reaction equation

HRID 52648 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][C:7]([CH3:10])([CH3:9])[O:8][C:4]=2[C:3]=1[C:13]#[N:14].[OH-:15].[K+].O>CC(O)(C)C>[NH2:14][C:13]([C:3]1[C:4]2[O:8][C:7]([CH3:10])([CH3:9])[CH2:6][C:5]=2[CH:11]=[CH:12][C:2]=1[Cl:1])=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 538583176-Chloro-7-cyano-2,3-dihydro-2,2-dimethylbenzofuran

Product 1

HCID 539852047-Aminocarbonyl-6-chloro-2,3-dihydro-2,2-dimethylbenzofuranYield 75.7%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A stirred solution of 10.0 grams (0.048 mole) of 6-chloro-7-cyano-2,3-dihydro-2,2-dimethylbenzofuran in 200 mL of 2-methyl-2-propanol was warmed to reflux, and 9.5 grams (0.17 mole) of 85% potassium hydroxide was added in one portion. Upon completion of addition, the reaction mixture was heated at reflux for about 75 minutes. The reaction mixture was then cooled and poured into 400 mL of water that was cooled in an ice bath. The resultant solid was collected by filtration and dried under vacuum, yielding 8.2 grams of 7-aminocarbonyl-6-chloro-2,3-dihydro-2,2-dimethylbenzofuran. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureto reflux
  2. additionUpon completion of addition
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for about 75 minutes
  5. temperatureThe reaction mixture was then cooled
  6. temperaturewas cooled in an ice bath
  7. filtrationThe resultant solid was collected by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-5848710eda984d9493a565b51dc463b4
Source dataset
uspto-grants-1997_04
Patent number
US05616718

Reaction notes

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