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

HRID 2357604
ノート
印刷プレビュー

反応式

HRID 2357604 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-d35ea5c11b8b40a495f52c0c093b7cd2
出典データセット
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07759337B2

反応ノート

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