Acetic Acid → 2-(1-neopentyl-2-oxo-2,3,4,7-tetrahydro-1H-pyrazolo[3,4-h]quinolin-3-yl)acetic acid

HRID 2378595

반응식

HRID 2378595 반응식
[NH2:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([CH2:6][CH:7]([CH2:19][C:20]([O:22]CC)=[O:21])[C:8](=[O:18])[N:9]2[CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.C(O)(=O)C.C(O[N:35]=O)CC(C)C.[OH-].[Li+]>C(Cl)(Cl)(Cl)Cl.ClCCl.O>[CH2:13]([N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]3[NH:1][N:35]=[CH:12][C:11]3=2)[CH2:6][CH:7]([CH2:19][C:20]([OH:22])=[O:21])[C:8]1=[O:18])[C:14]([CH3:15])([CH3:17])[CH3:16]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 8053Isoamyl NitriteHCID 59731974Ethyl 2-(7-amino-8-methyl-1-neopentyl-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetate

생성물 1

HCID 597319952-(1-neopentyl-2-oxo-2,3,4,7-tetrahydro-1H-pyrazolo[3,4-h]quinolin-3-yl)acetic acid

시약·촉매·용매 3

HCID 962Water용매HCID 5943Carbon Tetrachloride용매HCID 6344Dichloromethane용매

실험 절차

To a solution of ethyl 2-(7-amino-8-methyl-1-neopentyl-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetate (170 mg, 0.51 mmol) in carbon tetrachloride (4.5mL) was added acetic acid (0.5 mL) followed by isoamylnitrite (0.04 mL) and the reaction mixture was stirred for 2 h at room temperature. The reaction mixture was diluted with dichloromethane (40 mL), washed with aqueous NaHCO3 and dried. The solvent was removed and the crude product was dissolved in THF (15 mL) followed by addition of lithium hydroxide (43 mg, 1 mmol) and water (5 mL). After stirring for 12 h, the solvent was removed, acidified with 6 M HCl and extracted with ethyl acetate to give 2-(1-neopentyl-2-oxo-2,3,4,7-tetrahydro-1H-pyrazolo[3,4-h]quinolin-3-yl)acetic acid.

후처리

  1. washwashed with aqueous NaHCO3
  2. customdried
  3. customThe solvent was removed
  4. dissolutionthe crude product was dissolved in THF (15 mL)
  5. stirringAfter stirring for 12 h
  6. customthe solvent was removed
  7. extractionextracted with ethyl acetate

출처 및 근거

ORD 기록
ord-e2b781ca2a1b47b18ca1c57a8b98eb1d
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07470679B2

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