Thionyl Chloride → 4-(1-Chloroethyl)quinoline

HRID 1597364노트

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HRID 1597364 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11](O)[CH3:12])=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[Cl:16][CH:11]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1)[CH3:12]

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 53147551-(Quinolin-4-yl)ethanol

생성물 1

HCID 141713954-(1-Chloroethyl)quinoline수율 100%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
0 °C

실험 절차

To 1-Quinolin-4-yl-ethanol (1.4 g, 8.09 mmol) in 15 ml chloroform, thiony-chloride (1.8 ml, 20.2 mmol) was added dropwise over a five minute period at room temperature. Stirring was continued for 30 minutes after which the reaction mixture was cooled to 0° C. and quenched carefully by the addition of saturated aqueous NaHCO3 (20 ml). The chloroform layer was dried over sodium sulfate, filtered and concentrated. Column purification (hexane:ethyl acetate; 1.5:3.5) gave 1.54 g (100%) of the product as a syrup which was used as such for the subsequent step.

후처리

  1. customquenched carefully by the addition of saturated aqueous NaHCO3 (20 ml)
  2. dry with materialThe chloroform layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customColumn purification (hexane:ethyl acetate; 1.5:3.5)

출처 및 근거

ORD 기록
ord-1483d4265d4e4d3298d7d1030a129870
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06294566B1

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