Hydrochloric Acid → HCID 22408506, compound

HRID 2081683Notes

Reaction equation

HRID 2081683 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.[CH:16]([C:19]1[CH:24]=[CH:23][C:22]([NH:25]N)=[CH:21][CH:20]=1)([CH3:18])[CH3:17].Cl>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:25][C:22]3[CH:21]=[CH:20][C:19]([CH:16]([CH3:18])[CH3:17])=[CH:24][C:23]=3[C:7]=1[CH2:6]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2733248[4-(Propan-2-yl)phenyl]hydrazine hydrochlorideHCID 140321005-Methoxy-4,6-dimethyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 22408506HCID 22408506, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-methoxy-4,6-dimethyl-1-indanone (3.1 g, 16 mmol) and p-isopropylphenylhydrazine hydrochloride (3.05 g, 16 mmol), was heated to reflux in ethanol (20 cm3) containing concentrated hydrochloric acid (2 cm3). The reaction mixture was then heated at reflux for 4 hours and then allowed to cool to room temperature. The crystalline precipitate which formed, was filtered off, washed with 10% aqueous ethanol, and dried in a vacuum oven, to give the title compound as a pale green crystalline solid. Yield 3.04 g (62%). M.p. 130° C. (from ethanol). 1H NMR (CDCl3) δ: 1.33 (6H, d,), 2.34 (3H, s,), 2.35 (3H, s,), 3.02 (1H, septet,), 3.6 (1H, br,), 3.76 (2H, s,), 7.08 (1H, s,), 7.30 (1H, d,), 7.45 (1H, s,), 8.12 (1H, s,).

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was then heated
  3. temperatureat reflux for 4 hours
  4. customThe crystalline precipitate which formed
  5. filtrationwas filtered off
  6. washwashed with 10% aqueous ethanol
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-a52d62714aa54289992b2fdbfd59564f
Source dataset
uspto-grants-1993_02
Patent number
US05185360

Reaction notes

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