Hydrochloric Acid → HCID 15082719, compound

HRID 2081676Notes

Reaction equation

HRID 2081676 reaction equation
[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3]1.[C:12]1([NH:18]N)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>C(O)(=O)C>[CH3:1][CH:2]1[C:3]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[NH:18][C:4]=2[C:5]2[C:10]1=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 2595603-Methyl-indan-1-one

Product 1

HCID 15082719HCID 15082719, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Methyl-1-indanone (500 mg, 3,42 mmol) prepared by an analogous method to that described by A. M. Weidler et al., Acta Chem. Scand., 18 p. 148 (1964) and phenylhydrazine (0.35 cm3, 3.5 mmol), were heated to reflux in glacial acetic acid (20 cm3). After 2 minutes concentrated hydrochloric acid (1 cm3) was added down the reflux condenser. Boiling was continued for 75 minutes and then the reaction was cooled. The solution was poured into ice/water and extracted into ethyl acetate. The extracts were washed consecutively with brine and then water, and dried (MgSO4). Evaporation of solvent in vacuo, and column chromatography of the residue (10% EtOAc/petrol [60°-80° C.]) yielded the title compound as a cream solid. Yield: 320 mg (43%). M.p. 153°-155° C. 1H NMR (DMSO-d6) δ: 1.50 (3H, d,), 3.85 (1H, q.), 7.0-7.6 (8H, m.), 11.55 (1H, s,).

Workup

  1. temperaturethe reaction was cooled
  2. extractionextracted into ethyl acetate
  3. washThe extracts were washed consecutively with brine
  4. dry with materialwater, and dried (MgSO4)
  5. customEvaporation of solvent in vacuo, and column chromatography of the residue (10% EtOAc/petrol [60°-80° C.])

Sources & evidence

ORD record
ord-ca3cabcc2ca84016946cfb547c58dda6
Source dataset
uspto-grants-1993_02
Patent number
US05185360

Reaction notes

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