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

HRID 606312ノート

反応式

HRID 606312 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-430a20bdee074d54a2da199c33df1690
出典データセット
uspto-grants-2011_03
特許番号
US07915288B2

反応ノート

読み込み中…