Acetic Anhydride → HCID 53955654, compound

HRID 847505Notes

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

Participants

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

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