Hydrochloric Acid → HCID 18938337, compound

HRID 357675Notes

Reaction equation

HRID 357675 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[C:3]1=O.Cl>C1COCC1.CO>[CH3:1][C:2]1[CH2:10][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][C:8]=2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22172983HCID 22172983, compound

Product 1

HCID 18938337HCID 18938337, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

24.6 g (0.65 mol) of NaBH, were added in portions at 0° C. to a solution of 132 g (0.59 mol) of 2-methyl-4-(2-pyridyl)-1-indanone in 1000 cm3 of THF/methanol 2:1 and the mixture was stirred for 18 hours at room temperature. The reaction mixture was poured onto 1000 g of ice, admixed with concentrated aqueous HCl to a pH of 1 and extracted a number of times with Et2O. The combined organic phases were washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution. The solvent was removed under reduced pressure and the crude product was taken up in 1000 cm3 of toluene, admixed with 4.5 g of p-toluenesulfonic acid and heated under reflux for 2 hours using a water separator. Distillation at 0.1 mbar and 145° C. gave 84 g (69%) of 2-methyl-7-(2-pyridyl)indene as a colorless oil.

Workup

  1. extractionextracted a number of times with Et2O
  2. washThe combined organic phases were washed with saturated aqueous NaHCO3 solution and saturated aqueous NaCl solution
  3. customThe solvent was removed under reduced pressure
  4. temperatureheated
  5. temperatureunder reflux for 2 hours
  6. distillationDistillation at 0.1 mbar and 145° C.

Sources & evidence

ORD record
ord-257e378ee2364342bd8acaece6cd86c6
Source dataset
uspto-grants-1998_11
Patent number
US05840947

Reaction notes

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