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

HRID 1348922Notes

Reaction equation

HRID 1348922 reaction equation
[C:1]([N:4]1[C:13]2[CH:12]=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][C:8]=2[C:7]2[N:17]([C:25]3[CH:33]=[CH:32][C:28]4[O:29][CH2:30][O:31][C:27]=4[CH:26]=3)[N:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:6]=2[CH2:5]1)(=[O:3])[CH3:2]>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[C:1]([N:4]1[C:13]2[CH:12]=[CH:11][C:10]([NH2:14])=[CH:9][C:8]=2[C:7]2[N:17]([C:25]3[CH:33]=[CH:32][C:28]4[O:29][CH2:30][O:31][C:27]=4[CH:26]=3)[N:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 21092643ethyl 5-acetyl-1-(1,3-benzodioxol-5-yl)-8-nitro-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-3-carboxylate

Product 1

HCID 21092645ethyl 5-acetyl-8-amino-1-(1,3-benzodioxol-5-yl)-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-3-carboxylateYield 87%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

The material from Step 4 (930 mg, 0.00206 mol) was dissolved in acetic acid (25 mL), treated with a catalytic amount of 20% Pd(OH)2, and shaken for 12 hours, under 5 psi, at room temperature. The suspension was then filtered, and the filtrate was concentrated in vacuo to give the desired product as the acetic acid salt. 850 mg (MW=480.46, 87% yield). LC/MS m/z=421.6 (m+1).

Workup

  1. filtrationThe suspension was then filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-00d5104995a74b468e4d81e9bc417f8b
Source dataset
uspto-grants-2007_05
Patent number
US07211597B2

Reaction notes

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