Hydrochloric Acid → HCID 22408491, compound

HRID 2081691Notes

Reaction equation

HRID 2081691 reaction equation
[C:1]1(=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl.[CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21]N)([CH3:14])[CH3:13].Cl>C(O)C>[CH:12]([C:15]1[C:16]2[NH:21][C:1]3[C:9]4[C:4]([CH2:3][C:2]=3[C:17]=2[CH:18]=[CH:19][CH:20]=1)=[CH:5][CH:6]=[CH:7][CH:8]=4)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67351-IndanoneHCID 12292023[2-(Propan-2-yl)phenyl]hydrazine hydrochloride (1:1)

Product 1

HCID 22408491HCID 22408491, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 12.6 g (0.096 mol) of 1-indanone, 19.7 g (0.105 mol) of 2-isopropylphenylhydrazine hydrochloride, 150 ml of ethanol and 10 ml of conc. hydrochloric acid was refluxed for 2 hours. The solvent was removed by evaporation and the residue suspended in acidic water. Extraction with ether, drying (MgSO4) and evaporation gave the crude product, which was purified by column chromatography on silica gel using methylene chloride/light petroleum (2/8) as the eluant. The final purification was achieved by recrystallization from ethylacetate/light petroleum giving 14.0 g (59%) of the product. 1H NMR (CDCl3) 1.48 (6H, d), 3.37 (1H, septet), 3.77 (2H, s), 4.37 (1H, s), 7.1-7.3 (3H, m), 7.37 (1H, dd), 7.5-7.6 (3H, m), 8.03 (1H, s).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe solvent was removed by evaporation
  3. extractionExtraction with ether
  4. customdrying
  5. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-73d26a62eec544b486906b5a9c47a69b
Source dataset
uspto-grants-1993_02
Patent number
US05185360

Reaction notes

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