Sulfuric Acid → HCID 59140265, compound

HRID 2092356Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[C:12](=[C:13]4[CH:21]=[CH:20][CH:19]=[CH:18][C:14]4=[CH:15][CH:16]=3)[NH:11][C:10](=[O:22])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.N([O-])=O.[Na+].[N-:32]=[N+:33]=[N-].[Na+]>O.CO>[N:1]([C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[C:12](=[C:13]4[CH:21]=[CH:20][CH:19]=[CH:18][C:14]4=[CH:15][CH:16]=3)[NH:11][C:10](=[O:22])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1)=[N+:32]=[N-:33]

Participants

Conditions

Temperature: 0 °C

Procedure

4-(3-Amino-phenyl)-3,4-dihydro-1H-benzo[h]quinolin-2-one (0.29 g, 1 mmol) was dissolved in a mixture of con. sulfuric acid (2.5 ml), water (2.5 ml) and methanol (2.5 ml). The solution was stirred at 0° C. and a solution of sodium nitrite (0.83 g, 1.2 mmol) in water (1 ml) was slowly added. The solution was stirred at 0° C. for 0.5 hr and a solution of sodium azide (0.13 g, 2 mmol) in water (1 ml) was added. The mixture was stirred at 0° C. for 0.5 hr followed by overnight stirring at ambient temperature. Water was added and the precipitate separated by filtration. The product was purified by reverse phase HPLC (0.05 g, 0.15 mmol) (water-acetonitrile gradient, 0.05% formic acid, 90:10 to 10:90, 20 min, linear gradient; flow, 15 ml/min; column, Phenomenex Luna 5μ C18, 100×21.2 mm; UV 254 and 218 nm).

Workup

stirringThe solution was stirred at 0° C. for 0.5 hr
stirringThe mixture was stirred at 0° C. for 0.5 hr
stirringstirring at ambient temperature
customthe precipitate separated by filtration
customThe product was purified by reverse phase HPLC (0.05 g, 0.15 mmol) (water-acetonitrile gradient, 0.05% formic acid, 90:10 to 10:90, 20 min, linear gradient; flow, 15 ml/min; column, Phenomenex Luna 5μ C18, 100×21.2 mm; UV 254 and 218 nm)

Sources & evidence

ORD record: ord-ed9d5b23cdee42d7a9904f787f24d437
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440705B2

Reaction notes

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