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Acetic Anhydride → HCID 53955654, compound

HRID 847505
Notes
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Reaction equation

HRID 847505 reaction equation
C(OC(=O)C)(=O)C.O[CH:9]([C:25]1[C:26]([CH3:31])=[N:27][CH:28]=[CH:29][CH:30]=1)[CH:10]1[C:23](=[O:24])[N:14]2[C:15]3[C:20]([C:21]([CH3:22])=[C:13]2[CH2:12][CH2:11]1)=[CH:19][CH:18]=[CH:17][CH:16]=3>N1C=CC=CC=1>[CH3:22][C:21]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]2[C:23](=[O:24])[C:10](=[CH:9][C:25]3[C:26]([CH3:31])=[N:27][CH:28]=[CH:29][CH:30]=3)[CH2:11][CH2:12][C:13]=12
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 103361388,9-dihydro-7-[(hydroxy)(2-methylpyridin-3-yl)methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one

Product 1

HCID 53955654HCID 53955654, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

Acetic anhydride (2.24 g) was added to a solution of 8,9-dihydro-7-[(hydroxy)(2-methylpyridin-3-yl)methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one (1.35 g, a mixture of the isomers A and B) in pyridine (20 ml). After being stirred at 60° C. for 2 hours, the solution was evaporated in vacuo. The residue was diluted with chloroform, washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue and 1,8-diazabicyclo[5.4.0]undec-7-ene (1.27 g) were dissolved in toluene (30 ml). The solution was stirred at 60° C. for 2 hours and evaporated in vacuo. The residue was crystallized from ethyl acetate to give 8,9-dihydro-10-methyl-7-[(2-methylpyridin-3-yl)methylene]pyrido[1,2-a]-indol-6(7H)-one (0.92 g).

Workup

  1. customthe solution was evaporated in vacuo
  2. additionThe residue was diluted with chloroform
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. dissolutionThe residue and 1,8-diazabicyclo[5.4.0]undec-7-ene (1.27 g) were dissolved in toluene (30 ml)
  7. stirringThe solution was stirred at 60° C. for 2 hours
  8. customevaporated in vacuo
  9. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-886e549332af4752bdb07a6ffc9be055
Source dataset
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05141945

Reaction notes

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