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

HRID 2378595

反応式

HRID 2378595 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 5943Carbon Tetrachloride溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e2b781ca2a1b47b18ca1c57a8b98eb1d
出典データセット
uspto-grants-2008_12
特許番号
US07470679B2

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