Sulfuric Acid → HCID 178507166, compound

HRID 1175814Notes

Reaction equation

HRID 1175814 reaction equation
[NH2:1][C:2]1[N:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][C:11](N)=[CH:10][C:9]=3[NH:8][C:7](=[O:16])[C:6]=12.S(=O)(=O)(O)[OH:24].N([O-])=O.[Na+].C(=O)([O-])O.[Na+]>O.CO.C(OCC)(=O)C>[NH2:1][C:2]1[N:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([OH:24])=[CH:10][C:9]=3[NH:8][C:7](=[O:16])[C:6]=12

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 135599894HCID 135599894, compound

Product 1

HCID 178507166HCID 178507166, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture, which is cooled to 0° C., of 3,7-diamino-2-phenyl-2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one (100 mg), concentrated sulfuric acid (0.7 ml) and water (4 ml) was added dropwise a solution of sodium nitrite (46 mg) in water (1 ml), stirred at 0° C. for 30 minutes, at 90° C. for 1 hour and at room temperature for one night. The reaction mixture was neturalized by adding 5% sodium hydrogen carbonate, and ethyl acetate and methanol were added thereto. The insoluble materials were filtered off. The filtrate was extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography to obtain the target compound (18 mg).

Workup

  1. additionwere added
  2. filtrationThe insoluble materials were filtered off
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-92bd9c699da84525861a0ee20e5d0ccf
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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