Hydrochloric Acid → 1-(4-Aminophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 1904795Notes

Reaction equation

HRID 1904795 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]23[CH2:16][CH:15]2[C:14](=[O:17])[N:13]([CH3:18])[C:12]3=[O:19])=[CH:7][CH:6]=1)(=O)C.Cl.C(=O)(O)[O-].[Na+]>>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]23[CH2:16][CH:15]2[C:14](=[O:17])[N:13]([CH3:18])[C:12]3=[O:19])=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 200380371-(4-Acetylaminophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 101713541-(4-Aminophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane-2,4-dione

Conditions

Temperature
100 °C

Procedure

A mixture of 130 mg of 1-(4-acetylaminophenyl)-3-methyl-3-azabicyclo[3.1.0]hexane-2,4-dione and 1 ml of approx. 18% hydrochloric acid is stirred for about 4 hours at 100° C. The reaction mixture is adjusted at 0° C. to pH 9-10 with saturated aqueous sodium bicarbonate solution and extracted twice with ethyl acetate. The organic phases are washed until neutral with a small amount of water and a dilute solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated. Recrystallisation from ethyl acetate/petroleum ether affords the title compound which is identical with the title compound of Example 3(a).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic phases are washed until neutral with a small amount of water
  3. dry with materiala dilute solution of sodium chloride, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customRecrystallisation from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-47113a7658ef457fa338204073284d81
Source dataset
uspto-grants-1989_06
Patent number
US04839379

Reaction notes

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