Lithium hydroxide, monohydrate → 2-Methyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylic acid

HRID 1792787ノート

反応式

HRID 1792787 の反応式
O.[OH-].[Li+].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)[N:17]=[CH:16][CH:15]=2)[C:10]=1[CH3:24])=[O:8])C>O1CCCC1.O>[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)[N:17]=[CH:16][CH:15]=2)[C:10]=1[CH3:24])([OH:8])=[O:6]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 22024986Ethyl 2-methyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylate

生成物 1

HCID 220249512-Methyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylic acid収率 98.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

2.226 g (53 mmol) of lithium hydroxide monohydrate, in portions of 0.742 g every 24 hours, are added at 20° C. to 2.48 g (8.4 mmol) of 3-ethoxycarbonyl-2-methyl-1-(quinol-4-yl)-1H-pyrrole dissolved in 75 mL of tetrahydrofuran and 75 mL of water. After stirring at reflux for 72 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is taken up in 40 mL of water and then triturated with 10 mL of 5N hydrochloric acid for 0.2 hour. After filtering off and drying the solid residue under reduced pressure (2.7 kPa) at 40° C., 2.09 g of 3-carboxy-2-methyl-1-(quinol-4-yl)-1H-pyrrole are obtained in the form of a pinkish solid. Mass spectrum (EI): m/e 252 (M+.), m/e 207.

後処理

  1. temperatureat reflux for 72 hours
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customto give a residue which
  4. customtriturated with 10 mL of 5N hydrochloric acid for 0.2 hour
  5. filtrationAfter filtering off
  6. customdrying the solid residue under reduced pressure (2.7 kPa) at 40° C.

出典と根拠

ORDレコード
ord-116bbc84874e4ba3b9e0c615b3d8c0b2
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…