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

HRID 726609Notes

Reaction equation

HRID 726609 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 is warmed to reflux, and 9.5 grams (0.17 mole) of 85% potassium hydroxide is added in one portion. Upon completion of addition, the reaction mixture is heated at reflux for about 75 minutes. The reaction mixture is then cooled and poured into 400 mL of water that is cooled in an ice bath. The resultant solid is 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 is consistent with the proposed structure.

Workup

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

Sources & evidence

ORD record
ord-669efc88436d4553ab1c7e5af77e3a4c
Source dataset
uspto-grants-1998_01
Patent number
US05710157

Reaction notes

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