Formic Acid → HCID 89933024, compound

HRID 2207742Notes

Reaction equation

HRID 2207742 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([NH:11]N=C2CCCNC2=O)[CH:3]=1.[CH:20]([OH:22])=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:2]3[CH2:3][CH2:4][NH:11][C:20](=[O:22])[C:10]=3[NH:11]2)=[C:6]2[CH2:7][CH2:8][O:9][C:10]=12

Participants

3

Reactant 2

HCID 284Formic AcidHCID 123982390HCID 123982390, compound

Product 1

HCID 89933024HCID 89933024, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 3-[(7-chloro-2,3-dihydro-1-benzofuran-5-yl)hydrazinylidene]piperidin-2-one (a mixture of E and Z isomers) (3.66 g) and formic acid (65.4 mL) was stirred at 100° C. for 1 hour. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 95:5) to obtain an orange solid. This solid was washed with ethyl acetate to obtain a mixture (1.74 g) of 4-chloro-1,2,6,8,9,10-hexahydro-7H-furo[3,2-e]pyrido[3,4-b]indol-7-one and 10-chloro-2,3,5,7,8,9-hexahydro-6H-furo[2,3-f]pyrido[3,4-b]indol-6-one as an orange 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 column chromatography (chloroform:methanol=100:0 to 95:5)
  4. customto obtain an orange solid
  5. washThis solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-75c7a88176dc43458b74979cc92495e5
Source dataset
uspto-grants-2016_06
Patent number
US09376449B2

Reaction notes

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