Trifluoroacetic acid → HCID 9904040, compound

HRID 1822743Notes

Reaction equation

HRID 1822743 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:11]1[CH2:15][CH:14]=[CH:13][CH:12]=1.FC(F)(F)C(O)=O.[OH:23][CH2:24][C:25]([CH3:29])([CH3:28])[CH:26]=O>C(#N)C>[CH3:26][C:25]([CH:29]1[CH:13]2[CH2:14][CH:15]=[CH:11][CH:12]2[C:9]2[CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[NH:8]1)([CH3:28])[CH2:24][OH:23]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 74754-NitroanilineHCID 7612CyclopentadieneHCID 116993-Hydroxy-2,2-dimethylpropionaldehyde

Product 1

HCID 9904040HCID 9904040, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Nitroaniline (9.8 g), 6.5 ml of cyclopentadiene, and 5.5 ml of trifluoroacetic acid were dissolved in 70 ml of acetonitrile, and 10.0 g of hydroxypivalaldehyde was added at 0° C. After 30 minutes stirring at room temperature, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=1:1) to obtain 4.8 g of the captioned compound. Its physical properties are shown below.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-cb309a63e97c49998a677c7565dc3ae0
Source dataset
uspto-grants-2006_05
Patent number
US07037919B1

Reaction notes

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