4-Aminobenzoic Acid → Benzoic acid, 4-(phenylazo)-

HRID 843223Notes

Reaction equation

HRID 843223 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[N:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O>C(O)(=O)C>[C:13]1([N:11]=[N:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 11473Nitrosobenzene

Product 1

HCID 15276Benzoic acid, 4-(phenylazo)-Yield 72.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9.18 g (0.067 mol) of 4-aminobenzoic acid (Merck, purum) was placed in a 250 mL one-necked round flask with a magnetic stirring bar and 100 mL of glacial acetic acid was added causing a light yellow solution. After 20 minutes 7.21 g (0.067 mol) of nitrosobenzene (Fluka, purum) was added in one portion immediately forming a green solution with particles. Stirring at room temperature was continued for 16 h. The formed metal shining precipitate was filtered off and washed once with 50 mL of cold glacial acetic acid and twice with 100 mL of cold water. The orange precipitate was dissolve in a hot mixture of 200 mL of ethanol and 20 mL of water. After cooling, filtration and 15 h drying under vacuum at 60° C. 10.96 g (72% yield) of [4-(phenylazo)phenyl]-methanoic acid was obtained.

Workup

  1. customimmediately forming a green solution with particles
  2. filtrationwas filtered off
  3. washwashed once with 50 mL of cold glacial acetic acid and twice with 100 mL of cold water
  4. dissolutionThe orange precipitate was dissolve in a hot mixture of 200 mL of ethanol and 20 mL of water
  5. temperatureAfter cooling
  6. filtrationfiltration and 15 h
  7. customdrying under vacuum at 60° C

Sources & evidence

ORD record
ord-15d161e7f27e4ff9a142e33f181dcf05
Source dataset
uspto-grants-2002_04
Patent number
US06376655B1

Reaction notes

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