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

HRID 2378872Notes

Reaction equation

HRID 2378872 reaction equation
[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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

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 (4.5 mL) 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. MS (ESI) 316 (M+H); Rf=1.31.

Workup

  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

Sources & evidence

ORD record
ord-dbce23c526dd4bc6a5a397b3774ed887
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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