Methanol → 4,5,8,9-tetrahydro-8-phenyl-7H-thieno[3,2-a]quinolizin-7-one

HRID 477925Notes

Reaction equation

HRID 477925 reaction equation
[CH3:1][C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH2:5][CH2:4][N:3]=1.C=[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]1[CH2:18][C:19]([O:21]C)=O.[CH3:23]O>>[C:13]1([CH:18]2[CH2:23][CH:1]=[C:2]3[N:3]([CH2:4][CH2:5][C:6]4[S:10][CH:9]=[CH:8][C:7]=43)[C:19]2=[O:21])[CH:12]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 19020437Methyl 2-methylenephenylacetateHCID 218211774-methyl-6H,7H-thieno[3,2-c]pyridine

Product 1

HCID 190204044,5,8,9-tetrahydro-8-phenyl-7H-thieno[3,2-a]quinolizin-7-one

Procedure

A mixture of 20 g of 6,7-dihydro-4-methyl-thieno[3,2-c]pyridine and 19.8 g of methyl 2-methylenephenylacetate was heated under an argon atomosphere to 80° for 2 hours and subsequently to 110° for 48 hours. Methanol was added to the cooled reaction mixture and the product was left to crystallize out. There was obtained 4,5,8,9-tetrahydro-8-phenyl-7H-thieno[3,2-a]quinolizin-7-one of m.p. 159°-161°.

Workup

  1. temperaturewas heated under an argon atomosphere to 80° for 2 hours and subsequently to 110° for 48 hours
  2. waitthe product was left
  3. customto crystallize out

Sources & evidence

ORD record
ord-186c6f354d64409a86d01ceb4ac7bf1b
Source dataset
uspto-grants-1989_12
Patent number
US04889848

Reaction notes

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