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Hydrochloric Acid → 8-Chloro-2-(2-(quinolin-2-YL)ethyl)phthalazin-1(2H)-one

HRID 920920
ノート
印刷プレビュー

反応式

HRID 920920 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[N:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][C:33]=1[CH2:42][CH2:43]O.[Cl:45][C:46]1[CH:47]=[CH:48][CH:49]=[C:50]2[C:55]=1[C:54](=[O:56])[NH:53][N:52]=[CH:51]2.Cl>C1COCC1>[Cl:45][C:46]1[CH:47]=[CH:48][CH:49]=[C:50]2[C:55]=1[C:54](=[O:56])[N:53]([CH2:43][CH2:42][C:33]1[CH:34]=[CH:35][C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:32]=1)[N:52]=[CH:51]2
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 705322-QuinolineethanolHCID 5462977Diethyl azodicarboxylateHCID 713076628-Chloro-1(2H)-phthalazinone

生成物 1

HCID 717436398-Chloro-2-(2-(quinolin-2-YL)ethyl)phthalazin-1(2H)-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of triphenylphosphine (9.00 g, 34.3 mmol) in THF (100 mL), DEAD (5.44 mL, 34.3 mmol) was added at 0° C. After stirring for 15 min, 2-(quinolin-2-yl)ethanol from Example a1 (2.97 g, 17.17 mmol) was added. After another 15 min, 8-chlorophthalazin-1(2H)-one (3.1 g, 17.17 mmol) was added. The mixture was stirred overnight at room temperature; LC-MS indicated complete conversion to the product. 1 N HCl was added (pH=4). The mixture was extracted with EtOAc (3×50 mL), the EtOAc layers were discarded. The aqueous layer was neutralized by aq.NaHCO3 and extracted with ethyl acetate (3×500 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was suspended in EtOAc. The solid was filtered through a Büchner funnel. The purity of the title product was 95%.

後処理

  1. waitAfter another 15 min
  2. stirringThe mixture was stirred overnight at room temperature
  3. extractionThe mixture was extracted with EtOAc (3×50 mL)
  4. extractionNaHCO3 and extracted with ethyl acetate (3×500 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. filtrationThe solid was filtered through a Büchner funnel

出典と根拠

ORDレコード
ord-a7ca25ba64f14cc09726916b3f7c2876
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09273068B2

反応ノート

読み込み中…

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