Hydrochloric Acid → HCID 18938265, compound

HRID 357678Notes

Reaction equation

HRID 357678 reaction equation
[BH4-].[Na+].[CH3:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[C:13]2[CH:14]=[N:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:5]1=O.Cl>C1COCC1.CO>[CH3:3][C:4]1[CH2:12][C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][C:10]=2[C:13]1[CH:14]=[N:15][C:16]2[C:21]([CH:22]=1)=[CH:20][CH:19]=[CH:18][CH:17]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22173099HCID 22173099, compound

Product 1

HCID 18938265HCID 18938265, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

11.3 g (0.3 mol) of NaBH4 were added in portions at 0° C. to a solution of 64 g (0.23 mol) of 2-methyl-4-(3-quinolyl)-1-indanone in 600 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 2 g of p-toluenesulfonic acid and heated under reflux for 2 hours using a water separator. The reaction mixture was washed 3 times with 150 cm3 of saturated aqueous NaHCO3 solution and the solvent was removed under reduced pressure. Chromatography on silica gel (hexane/ethyl acetate 20:1) gave 45 g (76%) of 2-methyl-7-(3-quinolyl)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. washThe reaction mixture was washed 3 times with 150 cm3 of saturated aqueous NaHCO3 solution
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-82b18859823340458d7acad15d935e75
Source dataset
uspto-grants-1998_11
Patent number
US05840947

Reaction notes

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