Hydrochloric Acid → HCID 14032101, compound

HRID 2081681Notes

Reaction equation

HRID 2081681 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:14])=[C:5]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8](=O)[CH2:7][CH2:6]2.Cl.[C:16]1([NH:22]N)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl.O>C(O)C>[CH3:1][O:2][C:3]1[C:4]([CH3:14])=[C:5]2[C:9](=[CH:10][C:11]=1[CH3:12])[C:8]1[NH:22][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[C:7]=1[CH2:6]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 60962Phenylhydrazine hydrochlorideHCID 140321005-Methoxy-4,6-dimethyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 14032101HCID 14032101, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-methoxy-4,6-dimethyl-1-indanone (3.0 g, 16 mmol) and phenylhydrazine hydrochloride (2.3 g, 16 mmol) was heated to reflux in ethanol (20 cm3) containing concentrated hydrochloric acid (2 cm3). The reaction mixture was heated at reflux for 6 hours, and cooled to room temperature. Water was added, and the resulting precipitate filtered off. This product was dried in a vacuum oven, and purified by column chromatography to yield the title compound as a colourless solid. Yield: 2.8 g, (67%). M.p. 177° C. from ethyl acetate petrol (60°-80° C.). 1H NMR (CDCl3)δ: 2.36 (6H, s,), 3.56 (2H, s,), 3.76 (3H, s,), 7.1-7.6 (5H, m,), 8.2 (1H,br,).

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 6 hours
  4. filtrationthe resulting precipitate filtered off
  5. customThis product was dried in a vacuum oven
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-5c9ef2aee0604244bd283feed5706596
Source dataset
uspto-grants-1993_02
Patent number
US05185360

Reaction notes

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