Potassium Carbonate → 6-bromo-N-(2-(diethylamino)ethyl)phthalazin-1-amine

HRID 2357605Notes

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(=O)([O-])[O-].[K+].[K+].[CH2:19]([N:21]([CH2:25][CH3:26])[CH2:22][CH2:23][NH2:24])[CH3:20]>CN(C)C=O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([NH:24][CH2:23][CH2:22][N:21]([CH2:25][CH3:26])[CH2:19][CH3:20])=[N:7][N:6]=[CH:5]2

Participants

Conditions

Temperature: 80 °C

Procedure

6-Bromo-1-chlorophthalazine (0.22 g, 0.91 mmol) was dissolved in N,N-dimethylformamide (3 mL) and potassium carbonate (0.25 g, 1.81 mmol) and N1,N1-diethylethane-1,2-diamine (0.25 mL, 1.81 mmol) were added. The reaction mixture was heated to 80° C. for 5 h, cooled to ambient temperature and stirred for 16 h. The reaction mixture was diluted with 20 mL of EtOAc, added to an addition funnel and partitioned with sodium bicarbonate (saturated, aqueous). The organic layer was washed 3× with 20 mL of sodium bicarbonate (saturated, aqueous) and once with aqueous brine, separated, dried over sodium sulfate, and concentrated via rotovap to give crude product. The crude was purified by chromatography to obtain the title compound. Found MS (ES+): 323(M+H)+.

Workup

temperaturecooled to ambient temperature
additionadded to an addition funnel
custompartitioned with sodium bicarbonate (saturated, aqueous)
washThe organic layer was washed 3× with 20 mL of sodium bicarbonate (saturated, aqueous)
customonce with aqueous brine, separated
dry with materialdried over sodium sulfate
concentrationconcentrated via rotovap
customto give crude product
customThe crude was purified by chromatography

Sources & evidence

ORD record: ord-716d62a92dbf4913a5d22346c3782f3a
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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