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Potassium Carbonate → 6-Bromo-N-(2-(dimethylamino)ethyl)phthalazin-1-amine

HRID 2357604
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HRID 2357604 반응식
[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+].[CH3:19][N:20]([CH3:24])[CH2:21][CH2:22][NH2:23]>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:23][CH2:22][CH2:21][N:20]([CH3:24])[CH3:19])=[N:7][N:6]=[CH:5]2
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 66053N,N-DimethylethylenediamineHCID 220304246-Bromo-1-chlorophthalazine

생성물 1

HCID 684532906-Bromo-N-(2-(dimethylamino)ethyl)phthalazin-1-amine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

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-dimethylethane-1,2-diamine (0.20 mL, 1.81 mmol) was 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 3x 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+): 295(M+H)+.

후처리

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

출처 및 근거

ORD 기록
ord-d35ea5c11b8b40a495f52c0c093b7cd2
출처 데이터셋
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07759337B2

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