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Allyl bromide → 2-(Acetyl-allyl-amino)-6-chloroisonicotinic acid ethyl ester

HRID 1664218
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HRID 1664218 반응식
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[C:7]([NH:12][C:13](=[O:15])[CH3:14])[CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[CH:24]=[CH2:25]>CN(C=O)C.O.CC(OC)(C)C>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[C:7]([N:12]([C:13](=[O:15])[CH3:14])[CH2:25][CH:24]=[CH2:23])[CH:6]=1)[CH3:2]
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참가 물질

7

반응물 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 866204842-Acetylamino-6-chloroisonicotinic acid ethyl ester

생성물 1

HCID 866204832-(Acetyl-allyl-amino)-6-chloroisonicotinic acid ethyl ester

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide
용매
HCID 15413tert-Butyl methyl ether용매

반응 조건

온도
60 °C

실험 절차

A mixture of 6.0 g (25 mmol) 2-acetylamino-6-chloro-isonicotinic acid ethyl ester, 10.36 g (75 mmol) potassium carbonate and 4.23 ml (50 mmol) allyl bromide in 25 ml DMF is stirred at 60° C. for 24 h. The cooled mixture is diluted with water and TBME. The organic phase is washed with water, dried over Na2SO4 and evaporated. The product is purified by chromatography on silica gel (hexane/EtOAc 9/1) to yield the title compound as a yellowish oil.

후처리

  1. washThe organic phase is washed with water
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe product is purified by chromatography on silica gel (hexane/EtOAc 9/1)

출처 및 근거

ORD 기록
ord-84562b72ef1d4f4d813faf0271d36dbf
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08039455B2

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