Hydrochloric Acid → HCID 15082724, compound

HRID 2081677Notes

Reaction equation

HRID 2081677 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3]1.[C:13]1([NH:19]N)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl.O>C(O)(=O)C>[CH3:1][C:2]1([CH3:12])[C:3]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[NH:19][C:4]=2[C:5]2[C:10]1=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7516PhenylhydrazineHCID 3046283,3-Dimethyl-1-indanone

Product 1

HCID 15082724HCID 15082724, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3,3-dimethyl-1-indanone (20,0 q, 0,125 mol) prepared by the method described by R. Knorr et al., Leibig's Annalen, 1207 (1980) and phenylhydrazine (12.3 cm3, 0.125 mol) in glacial acetic acid (200 cm3), was heated to reflux. Concentrated hydrochloric acid (10 cm3) was added via the condenser, and boiling continued for a further 2 hours. The solution was allowed to cool, and then poured into water (500 cm3). The water was extracted with diethylether three times, the combined extracts were washed with brine and water, and dried (MgSO4). The solvent was removed, and petrol (60°-80° C.) added to the residue. The suspension was heated until boiling, The solid product was filtered off and the mother liquor concentrated. On cooling, more solid was obtained, and additional product separated out as the mother liquor was concentrated further. The solids were combined and crystallised from petrol to give the title compound. Yield: 10,2 g (35%). M.p. 160 ° C. 1H NMR: (CDCl3) δ: 1.60 (6H, s,), 7.1-7.7 (8H, m,), 8.16 (1H, s,).

Workup

  1. temperatureto cool
  2. extractionThe water was extracted with diethylether three times
  3. washthe combined extracts were washed with brine and water
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed
  6. additionpetrol (60°-80° C.) added to the residue
  7. temperatureThe suspension was heated until boiling
  8. filtrationThe solid product was filtered off
  9. concentrationthe mother liquor concentrated
  10. temperatureOn cooling
  11. custommore solid was obtained
  12. customadditional product separated out as the mother liquor
  13. concentrationwas concentrated further
  14. customcrystallised from petrol

Sources & evidence

ORD record
ord-2512620ed28d4aa88f2333412fd89bb5
Source dataset
uspto-grants-1993_02
Patent number
US05185360

Reaction notes

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