4-Tert-Butylaniline → (6-Bromo-phthalazin-1-yl)-(4-tert-butyl-phenyl)-amine

HRID 1791209Notes

Reaction equation

HRID 1791209 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](Cl)=[N:7][N:6]=[CH:5]2.[C:13]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14]>CC(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:21][C:20]1[CH:22]=[CH:23][C:17]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:18][CH:19]=1)=[N:7][N:6]=[CH:5]2

Participants

4

Reactant 2

HCID 698614-Tert-ButylanilineHCID 220304246-Bromo-1-chlorophthalazine

Product 1

HCID 22030046(6-Bromo-phthalazin-1-yl)-(4-tert-butyl-phenyl)-amine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Heat a mixture of 6-bromo-1-chloro-phthalazine (500 mg, 2.05 mmol) and 4-(tert-butyl)aniline (611 mg, 4.10 mmol) in 2-propanol (10 mL) at reflux for 3 hours. Evaporate the mixture, add 1M NaOH (10 mL), extract twice with EtOAc (10 mL each), dry (Na2SO4), and evaporate to provide the crude product. Purify by silica gel chromatography, eluting with dichloromethane followed by 95% CH2Cl2-MeOH to provide (6-Bromo-phthalazin-1-yl)-(4-tert-butyl-phenyl)-amine as a white solid.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 3 hours
  3. customEvaporate the mixture
  4. additionadd 1M NaOH (10 mL)
  5. extractionextract twice with EtOAc (10 mL each)
  6. dry with materialdry (Na2SO4)
  7. customevaporate
  8. customto provide the crude product
  9. customPurify by silica gel chromatography
  10. washeluting with dichloromethane

Sources & evidence

ORD record
ord-6ee57e5de1aa44ac9b53be26be235c4c
Source dataset
uspto-grants-2006_07
Patent number
US07074799B2

Reaction notes

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