Hydrochloric Acid → 1-Methyl-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one

HRID 1095354Notes

Reaction equation

HRID 1095354 reaction equation
C(Cl)(=O)C.[C:5]1([NH:11][NH2:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:13][C:14]1[NH:15][C:16]2[C:21]([C:22]=1[C:23](=O)[C:24]([O:26]CC)=O)=[CH:20][CH:19]=[CH:18][CH:17]=2.Cl>C(O)C.CO.C(O)(=O)C>[CH3:13][C:14]1[N:11]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:12]=[C:23]2[C:22]=1[C:21]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:15][C:24]2=[O:26]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 7516PhenylhydrazineHCID 246927Ethyl (2-methyl-1H-indol-3-yl)(oxo)acetate

Product 1

HCID 137937181-Methyl-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-oneYield 51.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Acetyl chloride (11.0 mL, 152 mmol), acetic acid (13 mL), and phenylhydrazine (15 mL, 152 mmol) were added sequentially to a suspension of ethyl (2-methyl-1H-indol-3-yl)(oxo)acetate (17 g, 76 mmol) in ethanol (380 mL). The reaction mixture was heated at reflux for 18 hours. After cooling to ambient temperature a red solid was isolated by filtration. The solid was boiled in a 1:1 mixture of 0.5 M hydrochloric acid and methanol and filtered to provide 10.8 g of 1-methyl-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one as a tan solid, mp>250° C. MS (APCI) m/z 276 (M+H)+; Anal. calcd for C17H13N3O: C, 74.17; H, 4.76; N, 15.26. Found: C, 73.95; H, 4.76; N, 15.04.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 hours
  3. customwas isolated by filtration
  4. filtrationfiltered

Sources & evidence

ORD record
ord-1671c4ba58ec4c1da9b433b063a65f9a
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

Loading…