(2H-1,3-Benzodioxol-5-yl)hydrazine--hydrogen chloride (1/1) → ethyl 5-acetyl-1-(1,3-benzodioxol-5-yl)-8-nitro-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-3-carboxylate

HRID 1348921Notes

Reaction equation

HRID 1348921 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.[O:26]1[C:30]2[CH:31]=[CH:32][C:33]([NH:35][NH2:36])=[CH:34][C:29]=2[O:28][CH2:27]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:35]([C:33]3[CH:32]=[CH:31][C:30]4[O:26][CH2:27][O:28][C:29]=4[CH:34]=3)[N:36]=[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 22291622(2H-1,3-Benzodioxol-5-yl)hydrazine--hydrogen chloride (1/1)HCID 58859529Ethyl (1-acetyl-6-nitro-4-oxo-1,2,3,4-tetrahydroquinolin-3-yl)(oxo)acetate

Product 1

HCID 21092643ethyl 5-acetyl-1-(1,3-benzodioxol-5-yl)-8-nitro-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-3-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

The material of Step 3 (1.1 g, 0.00331 mol) and 1-(1,3-benzodioxol-5-yl)hydrazine hydrochloride (500 mg, 0.00265 mol) were combined in acetic acid (10 mL) and heated to 60° C. for 5 hours. The suspension was then cooled and filtered to give the product as a brown solid. 930 mg (MW=450.4 g/mol, 78% yield). LC/MS m/z=451.5 (m+1).

Workup

  1. temperatureThe suspension was then cooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-a920323d7410465a9b5479cc98aec03f
Source dataset
uspto-grants-2007_05
Patent number
US07211597B2

Reaction notes

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