4-Aminophenol → HCID 3092593, compound

HRID 1413341Notes

Reaction equation

HRID 1413341 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[N+:9]([C:12]1[CH:22]=[CH:21][CH:20]=[C:14]2[C:15]([O:17][C:18](=O)[C:13]=12)=[O:16])([O-:11])=[O:10].O>C(O)(=O)C>[N+:9]([C:12]1[CH:22]=[CH:21][CH:20]=[C:14]2[C:15]([N:1]([C:2]3[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=3)[C:18](=[O:17])[C:13]=12)=[O:16])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 962WaterHCID 216313-Nitrophthalic anhydride

Product 1

HCID 3092593HCID 3092593, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The starting material used in the above example can be prepared as follows: 34.3 g (0.31 mol) of 4-aminophenol and 59.9 g (0.31 mol) of 3-nitrophthalic anhydride in 600 ml of acetic acid are refluxed for 6 hours and the mixture is then stirred into 3,000 ml of water. The product which has precipitated is washed with water and dried for 24 hours at 70° C./30 mm Hg. 69 g (78% of theory) of 4-(3-nitrophthalimidyl)-phenol are obtained; melting point 202° C. IR spectrum (KBr): 1785 cm-1 and 1725 cm-1 (CO--N--CO); 1550 and 1350 cm-1 (NO2).

Workup

  1. customcan be prepared
  2. customThe product which has precipitated
  3. washis washed with water
  4. customdried for 24 hours at 70° C./30 mm Hg

Sources & evidence

ORD record
ord-c88b943de0504852a59590627092eb94
Source dataset
uspto-grants-1981_02
Patent number
US04250096

Reaction notes

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