Acetic Anhydride → HCID 178476679, compound

HRID 477913Notes

Reaction equation

HRID 477913 reaction equation
OC[C:3]1[CH:4]=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:6](=[O:16])[N:7]2[C:12]=1[C:11]1[S:13][CH:14]=[CH:15][C:10]=1[CH2:9][CH2:8]2.[C:23]([O:26][C:27](=O)C)(=[O:25])[CH3:24]>N1C=CC=CC=1>[C:23]([O:26][CH2:27][SH:13]1[C:11]2[C:12]3[N:7]([CH2:8][CH2:9][C:10]=2[CH:15]=[CH:14]1)[C:6](=[O:16])[C:5]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[CH:4][CH:3]=3)(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 14666699HCID 14666699, compound

Product 1

HCID 178476679HCID 178476679, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of 1.55 g of 4,5-dihydro-10-(hydroxymethyl)-8-phenyl-7H-thieno[2,3-a]quinolizin-7-one in 6.7 ml of pyridine was treated with 3.35 ml of acetic anhydride while stirring, whereby a clear solution was obtained after about 15 minutes. After stirring overnight, the precipitated yellow crystals were removed by filtration under suction and washed with ether. The filtrate was evaporated in vacuo and the residue together with the above yellow crystals were recrystallized from methanol. There was obtained pure (4,5-dihydro-7-oxo-8-phenyl-thieno[2,3-a]-quinolizin-1-yl)methyl acetate of m.p. 145°-146°.

Workup

  1. customwhereby a clear solution was obtained after about 15 minutes
  2. stirringAfter stirring overnight
  3. customthe precipitated yellow crystals were removed by filtration under suction
  4. washwashed with ether
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue together with the above yellow crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-3900f27a04e544f58ba383f72b556d06
Source dataset
uspto-grants-1989_12
Patent number
US04889848

Reaction notes

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