Hydrochloric Acid → HCID 22173099, compound

HRID 357677Notes

Reaction equation

HRID 357677 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]2[CH:22]=[CH:21][CH:20]=[CH:19][C:12]=2[CH2:13][CH:14]([CH3:18])[C:15]([OH:17])=O)[CH:2]=1.S(Cl)(Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C1(C)C=CC=CC=1>[CH3:18][CH:14]1[CH2:13][C:12]2[C:19](=[CH:20][CH:21]=[CH:22][C:11]=2[C:3]2[CH:2]=[N:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:15]1=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 18938223HCID 18938223, compound

Product 1

HCID 22173099HCID 22173099, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 145 g (0.5 mol) of 2-(2-(3-quinolyl)benzyl)propionic acid in 119 g (1.0 mol) of thionyl chloride was stirred at room temperature for 18 hours. Excess thionyl chloride was removed at 10 mbar and the acid chloride was taken up in 400 cm3 of toluene. The solution was added dropwise at 10° C. to a suspension of 73 g (0.55 mol) of AlCl3 in 1000 cm3 of toluene and heated at 80° C. for 1 hour. The reaction mixture was poured onto 1000 g of ice and acidified with concentrated aqueous HCl to a pH of 1. The organic phase was separated off and the aqueous phase was further extracted 3 times with 200 cm3 each time of Et2O. The combined organic phases were washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution and subsequently dried (MgSO4). This gave 64 g (47%) of 2-methyl-4-(3-quinolyl)-1-indanone which was further reacted without further purification.

Workup

  1. customExcess thionyl chloride was removed at 10 mbar
  2. customThe organic phase was separated off
  3. extractionthe aqueous phase was further extracted 3 times with 200 cm3 each time of Et2O
  4. washThe combined organic phases were washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
  5. dry with materialsubsequently dried (MgSO4)
  6. customThis gave 64 g (47%) of 2-methyl-4-(3-quinolyl)-1-indanone which was further reacted without further purification

Sources & evidence

ORD record
ord-e7d6b6d0adc848399c6c40b45fde1b70
Source dataset
uspto-grants-1998_11
Patent number
US05840947

Reaction notes

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