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Sodium Iodide → 6-(1-Aziridinyl)-4-(3-chloro-4-fluoroanilino)-7-methoxy-3-quinolinecarbonitrile

HRID 548498
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HRID 548498 반응식
Cl[CH2:2][CH2:3][NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][C:9]([C:17]#[N:18])=[C:8]2[NH:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:4]1([C:5]2[CH:6]=[C:7]3[C:12](=[CH:13][C:14]=2[O:15][CH3:16])[N:11]=[CH:10][C:9]([C:17]#[N:18])=[C:8]3[NH:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([Cl:27])[CH:21]=2)[CH2:3][CH2:2]1
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참가 물질

5

반응물 3

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 216973236-[(2-Chloroethyl)amino]-4-(3-chloro-4-fluoroanilino)-7-methoxy-3-quinolinecarbonitrile

생성물 1

HCID 115597096-(1-Aziridinyl)-4-(3-chloro-4-fluoroanilino)-7-methoxy-3-quinolinecarbonitrile수율 103%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
75 °C

실험 절차

To a solution of 0.202 g (0.5 mmol) of 6-[(2-chloroethyl) amino]-4-(3-chloro-4-fluoroanilino)-7-methoxy-3-quinolinecarbonitrile in 4 ml of dimethylformamide, were added 0.075 g of sodium iodide (0.5 mmol) and 0.069 g of potassium carbonate (0.5 mmol). After the reaction solution was heated at 75° C. overnight, it was decanted into cold saturated sodium bicarbonate solution. The organic layer was separated and dried over sodium sulfate. The solvent was removed to yield 0.19 g of a light brown solid. The crude product was washed with hexane to give 0.1 g of a yellow solid, mp 197-199° C.; high resolution mass spectrometry (EI, m/e): M 368.0888.

후처리

  1. customit was decanted into cold saturated sodium bicarbonate solution
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed

출처 및 근거

ORD 기록
ord-fb722fc4f5304ddf88eb410ee3aad603
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
USRE042376E1

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