Trichloroacetic Acid → 3,4-Dihydro-5-methyl-1(2H)-isoquinolinone

HRID 1645906Notes

Reaction equation

HRID 1645906 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].ClC(Cl)(Cl)C(O)=O.[N-:19]=[N+]=[N-].[Na+]>>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:19][C:6]2=[O:11]

Participants

4

Reactant 3

HCID 6421Trichloroacetic AcidHCID 33557Sodium Azide2×HCID 44184314-Methyl-1-indanone

Product 1

HCID 1481403,4-Dihydro-5-methyl-1(2H)-isoquinolinoneYield 47.2%

Procedure

A mixture of 4.7 g (32.2 mmol) of 2,3-dihydro-4-methyl-1H-inden-1-one and 53 g of trichloroacetic acid was heated to 65°. To the resulting solution was added 4.2 g (64.4 mmol) of sodium azide and the mixture was kept at 65° for 18 hours. An additional 1.0 g of sodium azide was then added and heating continued for another four hours. The mixture was diluted with 200 ml of ice water and extracted with ether. The ether extracts were washed with water, saturated sodium hydrogen carbonate, dried (MgSO4), and concentrated. The residue was chromatographed (SiO2, ether to ether/methanol 95/5). The resulting product was recrystallized from toluene to give 2.45 g (47%) of product; mp 141°-143°.

Workup

  1. temperaturewas heated to 65°
  2. temperatureheating
  3. waitcontinued for another four hours
  4. extractionextracted with ether
  5. washThe ether extracts were washed with water, saturated sodium hydrogen carbonate
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was chromatographed (SiO2, ether to ether/methanol 95/5)
  9. customThe resulting product was recrystallized from toluene

Sources & evidence

ORD record
ord-004b3a8eb7984ec59b486de9877e9986
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

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