Sodium Hydroxide → 4-Methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acid

HRID 1710450ノート

反応式

HRID 1710450 の反応式
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[CH:10]=[C:11]3[C:18](=[O:19])[NH:17][CH2:16][CH:15]([CH3:20])[N:12]3[C:13]=2[CH:14]=1)=[O:5])C.[OH-].[Na+]>C1COCC1.CCO>[CH3:20][CH:15]1[N:12]2[C:13]3[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[CH:8][C:9]=3[CH:10]=[C:11]2[C:18](=[O:19])[NH:17][CH2:16]1

参加物

4

反応物 2

HCID 14798Sodium Hydroxide2 回HCID 67235749Ethyl 4-methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylate

生成物 1

HCID 587675714-Methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylic acid収率 77%

試薬・触媒・溶媒 1

HCID 21873804Tetrahydrofuran ethanol溶媒

反応条件

温度
75 °C

実験手順

To a suspension of ethyl ester from step d above (3.2 g, 11.75 mmol) in 100 mL of THF/EtOH (1:1 v/v) was added 1 N aq NaOH (43 mL, 43 mmol). The reaction mixture became a clear solution upon addition of 1 N NaOH. The clear solution was heated at 75° C. for 2 h. The reaction was concentrated and the crude residue was dissolved in water, and extracted with ether. The aqueous layer was acidified to pH ˜4 with 3 N HCl (˜16 mL). A large amount of white precipitate formed which was filtered off and rinsed with cold ether. The wet product was dried in the vacum oven (50° C.) to provide 2.2 g of 4-Methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid, yield 77% for two steps.

後処理

  1. concentrationThe reaction was concentrated
  2. dissolutionthe crude residue was dissolved in water
  3. extractionextracted with ether
  4. customA large amount of white precipitate formed which
  5. filtrationwas filtered off
  6. washrinsed with cold ether
  7. customThe wet product was dried in the vacum oven (50° C.)

出典と根拠

ORDレコード
ord-74332686b88e4961841adb7d2eaed21a
出典データセット
uspto-grants-2010_09
特許番号
US07790712B2

反応ノート

読み込み中…