Hydrochloric Acid → HCID 19780370, compound

HRID 2081680Notes

Reaction equation

HRID 2081680 reaction equation
Cl.[CH:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11]N)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[C:13]1(=O)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.Cl.C(O)C.O>C(O)C>[CH:2]([C:5]1[CH:10]=[CH:9][C:8]2[NH:11][C:15]3[C:16]4[C:21]([CH2:13][C:14]=3[C:7]=2[CH:6]=1)=[CH:20][CH:19]=[CH:18][CH:17]=4)([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 67351-IndanoneHCID 2733248[4-(Propan-2-yl)phenyl]hydrazine hydrochlorideHCID 19096565Water ethanol

Product 1

HCID 19780370HCID 19780370, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-isopropylphenylhydrazine hydrochloride (6.3 g, 34 mmol) and 1-indanone (4.5 g, 34 mmol) were heated to reflux in ethanol (40 cm3) containing concentrated hydrochloric acid (2 cm3). Heating was continued for 4 hours, and then the reaction mixture was cooled to room temperature during which time the product crystallised out of solution as colourless crystals. This compound was filtered off, dried in a vacuum oven, and recrystallised from ethanol/water to yield colourless prisms. Yield: 6.59 g, (79%). M.p. 193° C. (from ethanol/water). 1H NMR (DMSO-d6) δ: 1.27 (6H, d,), 2.96 (1H, septet,), 3.65 (2H, s,), 6.9-7.6 (7H, m,), 11.2 (1H, br,).

Workup

  1. temperaturewere heated
  2. temperatureHeating
  3. customcrystallised out of solution as colourless crystals
  4. filtrationThis compound was filtered off
  5. customdried in a vacuum oven
  6. customrecrystallised from ethanol/water
  7. customto yield colourless prisms

Sources & evidence

ORD record
ord-faef046dc33b49c3b9aa721af3bced62
Source dataset
uspto-grants-1993_02
Patent number
US05185360

Reaction notes

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