Hydrochloric Acid → 3,3-Dimethyl-1,3-dihydro-indol-2-one

HRID 74516Notes

Reaction equation

HRID 74516 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH3:14])([CH3:13])[C:5]1=[O:15])(=O)C.Cl.C(OC)(C)(C)C>O>[CH3:13][C:6]1([CH3:14])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][C:5]1=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15413tert-Butyl methyl etherHCID 8536071-Acetyl-3,3-dimethyl-1,3-dihydro-indol-2-one

Product 1

HCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.50 g (17.2 mmol) 1-acetyl-3,3-dimethyl-1,3-dihydro-indol-2-one were refluxed in 50 mL of a 6N hydrochloric acid solution for 1h. After cooling the reaction mixture was divided between tert-butylmethylether and water. The organic phase was washed with water, dried and evaporated down. The residue was crystallised from PE. The solid was suction filtered and dried at 80° C. in the CAD.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. washThe organic phase was washed with water
  3. customdried
  4. customevaporated down
  5. customThe residue was crystallised from PE
  6. filtrationfiltered
  7. customdried at 80° C. in the CAD

Sources & evidence

ORD record
ord-3fa64ecaaf0f4a5cbde8c460f74d2757
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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