3-(Chloromethyl)pyridine hydrochloride → 2-[5-Chloro-2-(pyridin-3-ylmethoxy)benzyl]isoindole-1,3-dione

HRID 392920

반응식

HRID 392920 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([CH:19]=1)[CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].Cl.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28]Cl)[CH:23]=1.[H-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH2:28][C:24]2[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=2)=[C:6]([CH:19]=1)[CH2:7][N:8]1[C:9](=[O:18])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]1=[O:17]

참가 물질

5

반응물 3

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 24758Sodium hydrideHCID 219732982-[5-Chloro-2-hydroxy benzyl]isoindole-1,3-dione

생성물 1

HCID 226617712-[5-Chloro-2-(pyridin-3-ylmethoxy)benzyl]isoindole-1,3-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-[5-chloro-2-hydroxy benzyl]isoindole-1,3-dione (300 mg, 1.04 mmol), and 3-picolylchloride hydrochloride (171 mg, 1.04 mmol) in anhydrous N,N-dimethylformamide (10 mL), cooled to 0° C., was added a 60% dispersion of sodium hydride in oil (104 mg, 2.6 mmol). The reaction was stirred at room temperature under anhydrous conditions for 15 h. The reaction was quenched by the addition of H2O (5 mL) and then poured into a separatory funnel, and aqueous saturated NaHCO3 solution (50 mL) was added. The aqueous layer was extracted 3×50 mL with CH2Cl2. The organics were combined and washed with saturated aqueous NaCl solution (100 mL), dried over MgSO4, filtered, and concentrated on a rotary evaporator triturated with ether, filtered and dried to yield the title compound.

후처리

  1. customThe reaction was quenched by the addition of H2O (5 mL)
  2. additionpoured into a separatory funnel
  3. additionaqueous saturated NaHCO3 solution (50 mL) was added
  4. extractionThe aqueous layer was extracted 3×50 mL with CH2Cl2
  5. washwashed with saturated aqueous NaCl solution (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated on a rotary evaporator
  9. customtriturated with ether
  10. filtrationfiltered
  11. customdried

출처 및 근거

ORD 기록
ord-65d39e7f9f4243bdaaafc34fa058d38b
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06803457B1

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