Water → 6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylic acid

HRID 42506ノート

反応式

HRID 42506 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:15]([O:17]C)=[O:16])[C:5]2[C:6]([CH3:14])=[CH:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[OH-].[Na+].O>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=[O:16])[C:5]2[C:6]([CH3:14])=[CH:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1

参加物

5

反応物 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67464634methyl 6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylate

生成物 1

HCID 674686786-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylic acid収率 89.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a stirred solution of methyl 6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylate (24 g, 77.4 mmol) in ethanol (400 mL) was added sodium hydroxide (4.02 g, 100.6 mmol), water (11 mL) and the mixture was stirred at reflux condition for 6 h. Ethanol was distilled off and residue was diluted with water, extracted with ethylacetate (40 mL) adjusted aqueous layer to PH-3 with 1N HCl and extracted with ethyl acetate (3×250 mL), finally organic layer was washed with brine solution, dried over anhydrous Na2SO4 and concentrated. The crude was washed with pet ether, filtered the solid and dried to afford desired product 6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylic acid (20.6 g, 89.8%).

後処理

  1. temperatureat reflux condition for 6 h
  2. distillationEthanol was distilled off
  3. additionresidue was diluted with water
  4. extractionextracted with ethylacetate (40 mL)
  5. extractionextracted with ethyl acetate (3×250 mL), finally organic layer
  6. washwas washed with brine solution
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. washThe crude was washed with pet ether
  10. filtrationfiltered the solid
  11. customdried

出典と根拠

ORDレコード
ord-5688b33536e4441d973ee67297f2ee28
出典データセット
uspto-grants-2013_09
特許番号
US08536179B2

反応ノート

読み込み中…