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

HRID 1178246Notes

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 creme-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 creme-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-39887c339be240d1842d1bae84063143
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07276505B2

Reaction notes

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