methyl 8-oxo-9-phenyl-8H-pyrido[1,2-d]thieno[2,3-f][1,4]thiazepin-11-carboxylate → methyl 7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylate

HRID 477945Notes

Reaction equation

HRID 477945 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[CH:9]S[C:11]3[CH:15]=[CH:14][S:13][C:12]=3[C:6]2=[C:5]([C:16]([O:18][CH3:19])=[O:17])[CH:4]=[C:3]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C(C)=CC=CC=1>[O:1]=[C:2]1[C:3]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:4][C:5]([C:16]([O:18][CH3:19])=[O:17])=[C:6]2[N:7]1[CH:8]=[CH:9][C:11]1[CH:15]=[CH:14][S:13][C:12]=12

Participants

3

Reactant 1

HCID 14666703methyl 8-oxo-9-phenyl-8H-pyrido[1,2-d]thieno[2,3-f][1,4]thiazepin-11-carboxylate

Product 1

HCID 14666705methyl 7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4.4 g of methyl 8-oxo-9-phenyl-8H-pyrido[1,2-d]thieno[2,3-f][1,4]thiazepine-11-carboxylate were heated under reflux and under argon together with 90 ml of xylene until the reaction was completed. The solution was evaporated in vacuo and the residue was treated with 100 ml of n-hexane, whereupon the product was removed by filtration. By recrystallization from ethyl acetate, there was obtained methyl 7-oxo-8-phenyl-7H-thieno[2,3-a]quinolizine-10-carboxylate as yellow crystals of m.p. 153°-156°.

Workup

  1. customThe solution was evaporated in vacuo
  2. additionthe residue was treated with 100 ml of n-hexane, whereupon the product
  3. customwas removed by filtration
  4. customBy recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-de7c74879ba14bd0b443914240e9938f
Source dataset
uspto-grants-1989_12
Patent number
US04889848

Reaction notes

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