Acetic Acid → HCID 178421668, compound

HRID 486190Notes

Reaction equation

HRID 486190 reaction equation
C(O)(=O)C.[CH3:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]2[C:15](=[O:44])[CH:16]([CH2:19][C:20]3[N:21]=[CH:22][N:23](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:24]=3)[CH2:17][CH2:18][C:7]=12>O>[NH:23]1[CH:24]=[C:20]([CH2:19][CH:16]2[C:15](=[O:44])[N:8]3[C:9]4[C:14]([C:6]([CH3:5])=[C:7]3[CH2:18][CH2:17]2)=[CH:13][CH:12]=[CH:11][CH:10]=4)[N:21]=[CH:22]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 10052431HCID 10052431, compound

Product 1

HCID 178421668HCID 178421668, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of acetic acid (50 ml) and water (15 ml), was added 8,9-dihydro-10-methyl-7-[(1-trityl-1H-imidazol-4-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (4.93 g), and stirred at 60° C. for 2 hours. After being cooled, the precipitates were filtered off. The filtrate was neutralized with aqueous 8N-sodium hydroxide solution, and extracted with chloroform. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was crystallized from diisopropyl ether-ethyl acetate (5:1, V/V) to give 8,9-dihydro-7-[(1H-imidazol-4-yl)methyl]-10-methylpyrido[1,2-a]indol-6(7H)-one (1.84 g).

Workup

  1. temperatureAfter being cooled
  2. filtrationthe precipitates were filtered off
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was crystallized from diisopropyl ether-ethyl acetate (5:1, V/V)

Sources & evidence

ORD record
ord-6a8de3914f8e4dbda02760916622fab5
Source dataset
uspto-grants-1994_03
Patent number
US05290785

Reaction notes

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