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

HRID 606303노트

반응식

HRID 606303 반응식
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Cl:12])=[N:4][C:3]=1[CH3:13].CN([CH:17]=[O:18])C>CCCCCC.C1COCC1>[Cl:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([CH:17]=[O:18])=[C:3]([CH3:13])[N:4]=1

참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 825722444-Bromo-1-chloro-3-methyl-isoquinoline

생성물 1

HCID 866159291-Chloro-3-methyl-isoquinoline-4-carbaldehyde수율 81%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

n-BiLi (12.3 ml of 1.6 M in hexane, 20 mmol) is added dropwise to a solution of 4-bromo-1-chloro-3-methyl-isoquinoline (4.6 g, 18 mmol) in THF (80 ml) at −78° C. and the mixture is stirred for 40 min. DMF (4.2 ml, 54 mmol) is then added slowly. The cold bath is removed, and stirring is continued for 15 min. The mixture is acidified with 1N—HCl to pH 2 and extracted with ether. The combined extracts are dried over Na2SO4 and concentrated in vacuo. The residue is chromatographed on silica gel to give 3.0 g of 1-chloro-3-methyl-isoquinoline-4-carbaldehyde. 1H NMR (CDCl3) 10.9 (s, 1H), 9.06 (d, 1H), 8.40 (d, 1H), 7.88 (t, 1H), 7.70 (t, 1H), 2.99 (s, 3H).

후처리

  1. customThe cold bath is removed
  2. stirringstirring
  3. waitis continued for 15 min
  4. extractionextracted with ether
  5. dry with materialThe combined extracts are dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on silica gel

출처 및 근거

ORD 기록
ord-f78d00767bec4bf2a2b72330d71cc318
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915288B2

반응 노트

불러오는 중…