Hydrochloric Acid → HCID 19780369, compound

HRID 2081685Notes

Reaction equation

HRID 2081685 reaction equation
[CH3:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([CH3:13])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=O.Cl.[CH3:16][C:17]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:18]=1[NH:24]N.Cl>C(O)C>[CH3:12][O:11][C:10]1[C:2]([CH3:1])=[C:3]2[C:7](=[CH:8][C:9]=1[CH3:13])[C:6]1[NH:24][C:18]3[C:17]([CH3:16])=[CH:22][C:21]([CH3:23])=[CH:20][C:19]=3[C:5]=1[CH2:4]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 140321005-Methoxy-4,6-dimethyl-2,3-dihydro-1H-inden-1-oneHCID 162130592,4-Dimethylphenylhydrazine hydrochloride

Product 1

HCID 19780369HCID 19780369, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4,6-Dimethyl-5-methoxy-1-indanone (2.2 g, 11.6 mmol) and 2,4-dimethylphenylhydrazine hydrochloride (2.00 g, 1 eq) were heated to reflux in ethanol (15 cm3) containing conc. HCl (1 cm3). After 2 hours, the precipitate was filtered and washed with ammonium hydroxide solution. All the collected material was extracted with ethyl acetate with the aid of salting out. The solvent was dried, and evaporated in vacuo and the product purified by column chromatography, eluting with 5% EtOAc/60°-80° petrol. The indole was recrystallised from dichloromethane/60°-80° petrol as pale beige needles. M.p. 210° C. 1H NMR (CDCl3)δ: 8.03 (1H, br), 7.25 (1H, s), 7.15 (1H, s), 6.81 (1H, s), 3.76 (3H, s), 3.53 (2H, s), 2.49 (3H, s), 2.43 (3H, s), 2.37 (6H, s).

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with ammonium hydroxide solution
  3. extractionAll the collected material was extracted with ethyl acetate with the aid
  4. customThe solvent was dried
  5. customevaporated in vacuo
  6. customthe product purified by column chromatography
  7. washeluting with 5% EtOAc/60°-80° petrol
  8. customThe indole was recrystallised from dichloromethane/60°-80° petrol as pale beige needles

Sources & evidence

ORD record
ord-d1ddc44b8af04af4b6f668f43b8778d9
Source dataset
uspto-grants-1993_02
Patent number
US05185360

Reaction notes

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