4-Hydrazinobenzoic acid → 4-(3-oxo-1,3-dihydro-2H-pyrazolo[4,3-c]cinnolin-2-yl)benzoic acid

HRID 1875467Notes

Reaction equation

[NH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)[NH2:2].Cl[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[N:15][C:14]=1[C:23](OC)=[O:24]>C(O)C>[O:24]=[C:23]1[C:14]2[N:15]=[N:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=3[C:13]=2[NH:2][N:1]1[C:3]1[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 47.5 °C

Procedure

4-Hydrazinobenzoic acid (68.4 mg, 0.45 mmol) was mixed at room temperature with ethanol (5 ml) to give a crème-coloured suspension. Methyl 4-chlorocinnoline-3-carboxylate (100 mg, 0.45 mmol) was added and the mixture was heated to 45-50° C. for 1 h. The reaction mixture was cooled to room temperature and the solvent was removed under vacuum. Ethyl acetate (10 ml) was added to the residue. The mixture was stirred at room temperature for 1 h. The solids were collected by filtration and dried under vacuum. The title compound was isolated as a brown powder (120 mg, 0.39 mmol, 86%). LCMS: m/z 307 [M+H]+. NMR [DMSO-d6]: δ=7.69-7.77 (m, 1Haryl); 7.81-7.90 (m, 2Haryl); 8.05 (d, J=8.85, 2Haryl); 8.20 (d, J=7.92 Hz, 1Haryl); 8.33 (d, J=8.85 Hz, 2Haryl); 14.64 (s, NH).

Workup

customto give a crème-coloured suspension
temperatureThe reaction mixture was cooled to room temperature
customthe solvent was removed under vacuum
additionEthyl acetate (10 ml) was added to the residue
filtrationThe solids were collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-ae32647676d9403896fefc92a0f0c1a8
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309552B2

Reaction notes

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