Dimethylformamide → 1-Chloro-6-methoxy-3-methyl-isoquinoline-4-carbaldehyde

HRID 606312노트

반응식

HRID 606312 반응식
[Li]CCCC.Br[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10]([Cl:19])=[N:9][C:8]=1[CH3:20].CN([CH:24]=[O:25])C>C1COCC1>[Cl:19][C:10]1[C:11]2[C:16](=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:7]([CH:24]=[O:25])=[C:8]([CH3:20])[N:9]=1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 866159324-Bromo-1-chloro-6-methoxy-3-methylisoquinolineHCID 178418339Butyllithium

생성물 1

HCID 866159331-Chloro-6-methoxy-3-methyl-isoquinoline-4-carbaldehyde수율 72.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

n-BuLi (12 ml of 1.6 M in hexane) is added dropwise to a solution of 4-bromo-1-chloro-6-methoxy-3-methyl-isoquinoline (4.8 g, 17 mmol) in THF (60 ml) at −78° C. After stirring for 40 min, DMF (4 ml, 51 mmol) is added slowly. The reaction is allowed to warm to 0° C. and the stirring is continued for 1 h. The mixture is then quenched with 1N—HCl (30 ml) and extracted with EtOAc. The combined extracts are dried over Na2SO4 and evaporated. The residue is chromatographed on silica gel eluting with EtOAc/hexane (1:4) to give 2.9 g of 1-chloro-6-methoxy-3-methyl-isoquinoline-4-carbaldehyde. 1H NMR (CDCl3) 10.8 (s, 1H), 8.61 (s, 1H), 8.24 (d, 1H), 7.29 (d, 1H), 4.01 (s, 3H), 2.99 (s, 3H).

후처리

  1. waitthe stirring is continued for 1 h
  2. customThe mixture is then quenched with 1N—HCl (30 ml)
  3. extractionextracted with EtOAc
  4. dry with materialThe combined extracts are dried over Na2SO4
  5. customevaporated
  6. customThe residue is chromatographed on silica gel eluting with EtOAc/hexane (1:4)

출처 및 근거

ORD 기록
ord-430a20bdee074d54a2da199c33df1690
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915288B2

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