4-Aminophenol → 4-((4-Phenylphthalazin-1-yl)amino)phenol

HRID 2361065Notes

Reaction equation

HRID 2361065 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:12][N:11]=1>C1C=CC=CC=1>[C:20]1([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=3)=[N:11][N:12]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 2721091-Chloro-4-phenylphthalazine

Product 1

HCID 28691684-((4-Phenylphthalazin-1-yl)amino)phenol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
100 °C

Procedure

A pressure bottle was charged with 4-aminophenol (0.453 g, 0.416 mmol), 1-chloro-4-phenylphthalazine (1.00 g, 0.416 mmol) and 16.8 mL of benzene. The bottle was sealed and heated to 100° C. for 25 h. The reaction mixture was concentrated. The crude material was dissolved in methanol and was purified by Gilson reverse phase liquid chromatography, 5-75% ACN/H2O/0.1% TFA over 14 min. The product-containing fractions were combined, brought to basic pH by addition of 1M NaHCO3, and extracted with dichloromethane. The organic portion was dried with MgSO4, filtered and concentrated to provide 4-(4-phenylphthalazin-1-ylamino)phenol as a yellow solid. MS m/z=314 [M+H]+. Calc'd for C20H15N3O: 313.35.

Workup

  1. customThe bottle was sealed
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionThe crude material was dissolved in methanol
  4. customwas purified by Gilson reverse phase liquid chromatography, 5-75% ACN/H2O/0.1% TFA over 14 min
  5. additionbrought to basic pH by addition of 1M NaHCO3
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic portion was dried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0a78a03def9a47ccb4d6ca60572fccba
Source dataset
uspto-grants-2014_04
Patent number
US08686155B2

Reaction notes

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