Acetic Anhydride → HCID 19913684, compound

HRID 477808Notes

Reaction equation

HRID 477808 reaction equation
[O:1]=[C:2]1[N:7]2[NH:8][CH2:9][C:10]3[CH:14]=[CH:13][S:12][C:11]=3[C:6]2=[C:5]([C:15]([O:17][CH3:18])=[O:16])[CH:4]=[C:3]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>>[C:25]([N:8]1[CH2:9][C:10]2[CH:14]=[CH:13][S:12][C:11]=2[C:6]2=[C:5]([C:15]([O:17][CH3:18])=[O:16])[CH:4]=[C:3]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:2](=[O:1])[N:7]12)(=[O:27])[CH3:26]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 19913661HCID 19913661, compound

Product 1

HCID 19913684HCID 19913684, compound

Procedure

0.54 g of methyl 4,5-dihydro-7-oxo-8-phenyl-7H-pyrido[1,2-b]thieno[2,3-d]pyridazine-10-carboxylate are suspended in 16 ml of acetic anhydride and heated to about 100° for 3 hours. The reaction solution is evaporated in vacuo and the residue is taken up in 32 ml of water and stirred up. The mixture is extracted twice with 30 ml of dichloromethane each time and once with 15 ml of dichloromethane. After drying over sodium sulfate, it is filtered and evaporated in vacuo. The residue is chromatographed on silica gel with dichloromethane/acetone (9:1). By recrystallization from ether there is obtained methyl 5-acetyl-4,5-dihydro-7-oxo-8-phenyl-7H-pyrido[1,2-b]thieno[2,3-d]pyridazine-10-carboxylate of m.p. 132°-134°.

Workup

  1. temperatureheated to about 100° for 3 hours
  2. customThe reaction solution is evaporated in vacuo
  3. extractionThe mixture is extracted twice with 30 ml of dichloromethane each time
  4. dry with materialAfter drying over sodium sulfate, it
  5. filtrationis filtered
  6. customevaporated in vacuo
  7. customThe residue is chromatographed on silica gel with dichloromethane/acetone (9:1)
  8. customBy recrystallization from ether

Sources & evidence

ORD record
ord-f5e39b1bfa004cd4b704746c7ca6d618
Source dataset
uspto-grants-1989_12
Patent number
US04889854

Reaction notes

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