4-Fluorophenylhydrazine hydrochloride → ethyl 5-acetyl-1-(4-fluorophenyl)-8-nitro-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-3-carboxylate

HRID 1348927Notes

Reaction equation

HRID 1348927 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=2)[C:7](=O)[CH:6]([C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:5]1)(=[O:3])[CH3:2].Cl.[F:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][NH2:34])=[CH:29][CH:28]=1>C(O)(=O)C>[C:1]([N:4]1[C:13]2[CH:12]=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=2[C:7]2[N:33]([C:30]3[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=3)[N:34]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 58859529Ethyl (1-acetyl-6-nitro-4-oxo-1,2,3,4-tetrahydroquinolin-3-yl)(oxo)acetate

Product 1

HCID 21092644ethyl 5-acetyl-1-(4-fluorophenyl)-8-nitro-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-3-carboxylateYield 59%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The material of step 3 of Example 17 (15 g, 0.044 mol) was dissolved in 100 mL of glacial acetic acid and then 4-fluorophenyl hydrazine hydrochloride (7.15 g, 0.044 mol) was added. The reaction was then stirred at room temperature for 18 hours, under argon, and then concentrated to remove most of the acetic acid. The remaining viscous oil was triturated with 250 mL acetonitrile. The resulting solid was isolated by vacuum filtration and dried to yield the product as an orange/pink solid. 11 g (MW=424.38, 59% yield). LC/MS m/z=425.2 (m+1).

Workup

  1. concentrationconcentrated
  2. customto remove most of the acetic acid
  3. customThe remaining viscous oil was triturated with 250 mL acetonitrile
  4. customThe resulting solid was isolated by vacuum filtration
  5. customdried

Sources & evidence

ORD record
ord-c0887708c4e246f7a65a853ac2f266b7
Source dataset
uspto-grants-2007_05
Patent number
US07211597B2

Reaction notes

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