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

HRID 1710450노트

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HRID 1710450 반응식
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

참가 물질

4

반응물 2

HCID 14798Sodium Hydroxide2회HCID 67235749Ethyl 4-methyl-1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-7-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 21873804Tetrahydrofuran ethanol용매

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온도
75 °C

실험 절차

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.

후처리

  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.)

출처 및 근거

ORD 기록
ord-74332686b88e4961841adb7d2eaed21a
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790712B2

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