Formic Acid → HCID 616433, compound

HRID 1775433Notes

Reaction equation

HRID 1775433 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:10]N=C2CCCNC2=O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH:19]([OH:21])=O>O>[F:1][C:2]1[CH:3]=[C:4]2[C:5]([C:2]3[CH2:3][CH2:4][NH:10][C:19](=[O:21])[C:7]=3[NH:10]2)=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 73849142HCID 73849142, compound

Product 1

HCID 616433HCID 616433, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-[(3-fluoro-4-methoxyphenyl)hydrazinylidene]piperidin-2-one (a mixture of E and Z isomers) (2.45 g) and formic acid (25.0 mL) was stirred at 100° C. for 1 hour. The reaction mixture was cooled to room temperature, and then water (40.0 mL) was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The insoluble materials were separated by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol=10:0 to 10:1) to obtain 7-fluoro-6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one (780 mg) as a brown solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe insoluble materials were separated by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform:methanol=10:0 to 10:1)

Sources & evidence

ORD record
ord-6a16d83ed97349daa1f0f24e651e6eba
Source dataset
uspto-grants-2016_02
Patent number
US09260445B2

Reaction notes

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