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

HRID 1348931Notes

Reaction equation

C([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:17]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[N:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:6]=2[CH2:5]1)(=O)C>CCO.Cl>[F:31][C:28]1[CH:29]=[CH:30][C:25]([N:17]2[C:7]3[C:8]4[CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:12][C:13]=4[NH:4][CH2:5][C:6]=3[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:18]2)=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The material from step 1 of Example 24 (5 g, 0.0117 mol) was suspended in 100 mL absolute EtOH and 60 mL 1N HCl. The mixture was then heated to 80° C. for 18 hours. The heating was then terminated and the compound filtered upon cooling, to give the pure desired product as an orange solid. 3.8 g. (MW=382.35, 85% yield). LC/MS m/z=383.4 (m+1).

Workup

customThe heating was then terminated
filtrationthe compound filtered
temperatureupon cooling

Sources & evidence

ORD record: ord-78a855c5778e44c9b0c69ff75ff3ecd9
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07211597B2

Reaction notes

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