Water → 1-(Isoquinolin-4-yl)-1H-pyrrole-3-carboxylic acid

HRID 1792802ノート

反応式

HRID 1792802 の反応式
O.[OH-].[Li+].O.C[O:6][C:7]([C:9]1[CH:13]=[CH:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[N:16][CH:15]=2)[CH:10]=1)=[O:8].[K+].[Br-]>O1CCCC1>[C:7]([C:9]1[CH:13]=[CH:12][N:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[N:16][CH:15]=2)[CH:10]=1)([OH:8])=[O:6]

参加物

6

反応物 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 253877Potassium BromideHCID 22024992Methyl 1-(isoquinolin-4-yl)-1H-pyrrole-3-carboxylate

生成物 1

HCID 220249401-(Isoquinolin-4-yl)-1H-pyrrole-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

0.63 g (15.02 mmol) of lithium hydroxide monohydrate and 20 mL of water are added to a solution, at a temperature in the region of 22° C., of 0.95 g (376 mmol) of 3-methoxycarbonyl-1-(isoquinol-4-yl)-1H-pyrrole in 20 mL of tetrahydrofuran. After stirring at the reflux point of the solvent for 15 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) and the residue is dissolved in water. The solution is extracted with ethyl acetate and the organic phase is discarded. The aqueous phase is adjusted to pH 6 with N hydrochloric acid and extracted with ethyl acetate. The organic phase is washed successively with water and with saturated aqueous sodium chloride solution and then it is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa), resulting in 0.75 g of 3-carboxy-1-(isoquinol-4-yl)-1H-pyrrole in the form of a beige-coloured solid. IR spectrum (KBr): 3153, 2518, 1855, 1690, 1495, 1276, 1188, 933, 808, 783, 757, 712 and 675 cm−1.

後処理

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. dissolutionthe residue is dissolved in water
  3. extractionThe solution is extracted with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic phase is washed successively with water and with saturated aqueous sodium chloride solution
  6. dry with materialit is dried over magnesium sulphate
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  8. customresulting in 0.75 g of 3-carboxy-1-(isoquinol-4-yl)-1H-pyrrole in the form of a beige-coloured solid

出典と根拠

ORDレコード
ord-a71ed9b08627498493d90473bab0af9f
出典データセット
uspto-grants-2006_07
特許番号
US07078414B2

反応ノート

読み込み中…