Sodium Methoxide → HCID 14770035, compound

HRID 648525Notes

Reaction equation

HRID 648525 reaction equation
[N+:1]([CH:4]1[C:13]23S[C:6]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)([C:7](=[O:18])[N:8]2[CH2:9][CH2:10][C:11]2[CH:17]=[CH:16][S:15][C:12]=23)[CH2:5]1)([O-:3])=[O:2].C[O-].[Na+]>CO>[N+:1]([C:4]1[CH:5]=[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7](=[O:18])[N:8]2[C:13]=1[C:12]1[S:15][CH:16]=[CH:17][C:11]=1[CH2:10][CH2:9]2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 19020424HCID 19020424, compound

Product 1

HCID 14770035HCID 14770035, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.58 g of 4,5,9,10-tetrahydro-10-nitro-8-phenyl-8,10a-epithio-10aH-thieno[2,3-a]quinolizin-7(8H)-one were heated slowly together with 2 equivalents of sodium methylate in 30 ml of methanol. After the reaction ceases, the mixture was heated under reflux for an additional 2 hours, whereupon the solvent was removed by distillation and the residue was chromatographed on silica gel with toluene/acetone (9:1). There was obtained 4,5-dihydro-10-nitro-8-phenyl-7H-thieno[2,3-a]quinolizin-7-one of m.p. 186°-189° (from acetonitrile) and in a later fraction 10-amino-4,5-dihydro-8-phenyl-7H-thieno[2,3-a]quinolizin-7-one of m.p. 180.5°-181.5° (from toluene).

Workup

  1. customAfter the reaction ceases
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for an additional 2 hours, whereupon the solvent
  4. customwas removed by distillation
  5. customthe residue was chromatographed on silica gel with toluene/acetone (9:1)

Sources & evidence

ORD record
ord-53a6b0d3d80d41c9a492a0891e8571ab
Source dataset
uspto-grants-1988_04
Patent number
US04735940

Reaction notes

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