4-Nitrophenol → HCID 86741763, compound

HRID 2308596Notes

Reaction equation

HRID 2308596 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH2:10][C:11]2([OH:19])[C:16]([OH:18])=[O:17])=[O:4].[CH:22]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[C:24](O)[CH:23]=1.CN(C)C=O.S(Cl)(Cl)=O>C(#N)C>[F:1][C:2]([F:20])([F:21])[C:3]([NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH2:10][C:11]2([OH:19])[C:16]([O:18][C:24]1[CH:23]=[CH:22][C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=1)=[O:17])=[O:4]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 86741764HCID 86741764, compound

Product 1

HCID 86741763HCID 86741763, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 1.5 liters of acetonitrile were dispersed 200 g of 5-trifluoroacetamido-1-hydroxynaphthoic acid and 100 g of p-nitrophenol, and the mixture was stirred under heating. To the dispersion was added 15 ml of dimethylformamide, and 110 ml of thionyl chloride was added thereto dropwise. After the dropwise addition, the mixture was heated while stirring for 1 hour, followed by cooling. The precipitate thus formed was collected by filtration, washed with acetonitrile, and dried to obtain 230 g of p-nitrophenyl 5-trifluoroacetamido-1-hydroxynaphthoate.

Workup

  1. temperatureunder heating
  2. additionwas added
  3. additionAfter the dropwise addition
  4. temperaturethe mixture was heated
  5. stirringwhile stirring for 1 hour
  6. temperatureby cooling
  7. customThe precipitate thus formed
  8. filtrationwas collected by filtration
  9. washwashed with acetonitrile
  10. customdried

Sources & evidence

ORD record
ord-f538aa760b3447d88628a5b51611aca0
Source dataset
uspto-grants-1987_09
Patent number
US04690889

Reaction notes

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