2,3-Bishydrazinocarbonyl-5-bromo-7-ethyl-4-hydroxyquinoline → HCID 178418252, compound

HRID 1451303Notes

Reaction equation

[NH:1]([C:3]([C:5]1[C:14]([C:15]([NH:17]N)=[O:16])=[C:13]([OH:19])[C:12]2[C:7](=[CH:8][C:9]([CH2:21][CH3:22])=[CH:10][C:11]=2[Br:20])[N:6]=1)=[O:4])N>C(O)(=O)C>[Br:20][C:11]1[C:12]2[C:13]([OH:19])=[C:14]3[C:15](=[O:16])[NH:17][NH:1][C:3](=[O:4])[C:5]3=[N:6][C:7]=2[CH:8]=[C:9]([CH2:21][CH3:22])[CH:10]=1

Participants

Conditions

Temperature: 81 °C

Procedure

A stirred mixture of 2,3-bishydrazinocarbonyl-5-bromo-7-ethyl-4-hydroxyquinoline (0.40 g, 1.1 mM) in glacial acetic acid (12 mL) was heated at 81° C. for 1.5 hr. After cooling to room temperature, the reaction mixture was filtered and the collected solids washed with acetic acid and air dried to provide the title compound (0.25 g, 70%) as a light brown solid, mp >400° C.; MS(CI): 336 (M+H). Analysis for C13H10BrN3O3 ·0.13 CH3CO2H Calculated: C, 46.31; H, 3.08; N, 12.21 Found: C, 46.50; H, 3.32; N, 12.19

Workup

temperatureAfter cooling to room temperature
filtrationthe reaction mixture was filtered
washthe collected solids washed with acetic acid and air
customdried

Sources & evidence

ORD record: ord-4b0662c4ed83433bbf1ed5224e5a8562
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05604227

Reaction notes

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