Acetic Acid → HCID 89933015, compound

HRID 2207740Notes

Reaction equation

HRID 2207740 reaction equation
[Br:1][C:2]1[C:10]([NH:11]N=C2CCCNC2=O)=[CH:9][C:5]2[CH2:6][CH2:7][O:8][C:4]=2[CH:3]=1.[C:20]([OH:23])(=O)[CH3:21]>>[Br:1][C:2]1[CH:3]=[C:4]2[O:8][CH2:7][CH2:6][C:5]2=[C:9]2[C:10]=1[NH:11][C:21]1[C:20](=[O:23])[NH:11][CH2:10][CH2:9][C:5]2=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 123387838HCID 123387838, compound

Product 1

HCID 89933015HCID 89933015, compound

Conditions

Temperature
115 °C

Procedure

A mixture of 3-[(6-bromo-2,3-dihydro-1-benzofuran-5-yl)hydrazinylidene]piperidin-2-one (a mixture of E and Z isomers)(137 mg) and acetic acid (3.00 mL) was stirred at 115° C. for 4 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel chromatography (chloroform:methanol=100:0 to 96:4) to obtain 5-bromo-1,2,6,8,9,10-hexahydro-7H-furo[3,2-e]pyrido[3,4-b]indol-7-one (40.0 mg) as a red solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel chromatography (chloroform:methanol=100:0 to 96:4)

Sources & evidence

ORD record
ord-0112a7ca52714ad0acbf0fda4a28a2fb
Source dataset
uspto-grants-2016_06
Patent number
US09376449B2

Reaction notes

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