4-Aminophenol → HCID 23437540, compound

HRID 1648943Notes

Reaction equation

HRID 1648943 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:9]1(=[O:15])O[C:12](=[O:13])[CH:11]=[CH:10]1.C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+].C[N:29](C=O)C>>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]2[C:9]([NH:29][C:12](=[O:13])[CH:11]=2)=[O:15])=[CH:3][CH:4]=1

Participants

6

Reactant 5

HCID 4034-AminophenolHCID 6228Dimethylformamide2×HCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 517045Sodium Acetate

Product 1

HCID 23437540HCID 23437540, compound

Conditions

Temperature
50 °C

Procedure

To a solution under dry N2 of 54.56 grams para aminophenol (0.5 mole) at 25 percent solids in DMF, add a soluion of 49.03 grams maleic anhydride (0.5 mole) at 50 percent solids in DMF at a rate sufficient to keep the temperature below 70° C. Stir solution 15 minutes. Add 122.51 grams acetic anhydride (1 mole+20% molar excess) and 9.84 grams sodium acetate (0.1 mole+20% molar excess). Heat the resulting mixture to 50° C. and maintain for 1.5 hours. At this point, the whole mass yields a yellow precipitate. Filter the cool precipitate, wash well with water, dry in vacuum oven at 40° C. overnight. The product achieved has a melting point of 158°-162° C.

Workup

  1. customthe temperature below 70° C
  2. customStir solution 15 minutes
  3. temperaturemaintain for 1.5 hours
  4. customAt this point, the whole mass yields a yellow precipitate
  5. filtrationFilter the cool precipitate
  6. washwash well with water
  7. customdry in vacuum oven at 40° C. overnight

Sources & evidence

ORD record
ord-074945a1d2cb49d5babee6116bfd0662
Source dataset
uspto-grants-1983_11
Patent number
US04414269

Reaction notes

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