Nitrosobenzene → 3517-23-5

HRID 843224Notes

Reaction equation

HRID 843224 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[N:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O>C(O)(=O)C>[C:14]1([N:12]=[N:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 11473NitrosobenzeneHCID 145334-Aminophenylacetic acid

Product 1

HCID 2464713517-23-5Yield 45%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

10.13 g (0.067 mol) of 4-aminophenylacetic acid Merck, pro analysis) was placed in a 250 mL one-necked round flask with a magnetic stirring bar and 100 mL of glacial acetic acid was added; during 15 minutes a light yellow suspension was formed. 7.22 g (0.067 mol) of nitrosobenzene (Fluka, purum) was added rapidly resulting in a green suspension. Stirring at room temperature was continued for 18 h. The resulting metallic shining needles in a brown solution was vacuum filtered and washed once with 50 mL of cold glacial acetic acid and five times with 50 mL portions of cold water. The orange precipitate was dissolved by heating to boiling in a mixture of 160 mL of ethanol and 40 mL of water. After unforced cooling to room temperature the mixture was cooled on an ice/water bath and vacuum filtered. The filtercake was washed six times with 25 mL of externally cooled ethanoL After drying 16 h at 50° C. under vacuum 7.23 g (yield 45%) of 2-[4(phenylazo)phenyl]-ethanoic acid was obtained.

Workup

  1. customduring 15 minutes a light yellow suspension was formed
  2. customresulting in a green suspension
  3. filtrationfiltered
  4. washwashed once with 50 mL of cold glacial acetic acid and five times with 50 mL portions of cold water
  5. dissolutionThe orange precipitate was dissolved
  6. temperatureby heating
  7. additionto boiling in a mixture of 160 mL of ethanol and 40 mL of water
  8. temperatureAfter unforced cooling to room temperature the mixture
  9. temperaturewas cooled on an ice/water bath
  10. filtrationvacuum filtered
  11. washThe filtercake was washed six times with 25 mL of externally cooled ethanoL

Sources & evidence

ORD record
ord-8657c495fe8141b5a52be137c18a41e0
Source dataset
uspto-grants-2002_04
Patent number
US06376655B1

Reaction notes

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