Hydrochloric Acid → 7-Amino-2-Isopropyl-4-bromo-2H-phthalazin-1-one

HRID 1783657Notes

Reaction equation

HRID 1783657 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8]([Br:18])=[N:9][N:10]([CH:15]([CH3:17])[CH3:16])[C:11]2=[O:14])=[CH:6][CH:5]=1)([O-])=O.Cl>CCO.O.[Fe]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([Br:18])=[N:9][N:10]([CH:15]([CH3:16])[CH3:17])[C:11]2=[O:14])=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 211065877-Nitro-2-Isopropyl-4-bromo-2H-phthalazin-1-one

Product 1

HCID 211065807-Amino-2-Isopropyl-4-bromo-2H-phthalazin-1-oneYield 99.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

7-Nitro-2-Isopropyl-4-bromo-2H-phthalazin-1-one (4.6 g, 0.015 mol) was dissolved in a 5:1 mixture of EtOH and water (150 ml). To this solution was added iron powder (2.14 g, 0.039 mol) and concentrated HCl (1 ml), the mixture was heated to 80° C. for three hours. After this time, the reaction mixture was cooled to RT and filtered through a pad of celite, the celite was washed with EtOH (100 ml), and the solution was concentrated under vacuum to give the title compound (4.2 g, 98% yield) as a white solid. 1H-NMR: (400 MHz, D6-DMSO), 7.56 (1H, d), 7.28 (1H, s), 7.13 (1 H, d), 6.47 (2H, s), 5.24-5.09 (1H, m), 1.23 (6H, d); MS (ESI+)=(M+H)+ 282, 284

Workup

  1. temperatureAfter this time, the reaction mixture was cooled to RT
  2. filtrationfiltered through a pad of celite
  3. washthe celite was washed with EtOH (100 ml)
  4. concentrationthe solution was concentrated under vacuum

Sources & evidence

ORD record
ord-00e3a981a4f744c4b8c8a283b4d93bc2
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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