Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | Sodium Nitrite | HCID 23668193 | — |
| Reactant | HCID 66700259 | HCID 66700259 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Product | HCID 58362457 | HCID 58362457 | 93.4% |
Reaction Steps
T446 To a solution of 4-(quinolin-2-yl)aniline dihydrochloride (29.0 mg, 0.1 mmol) in 1 N HCl (1 mL) was added NaNO2 solution (7.0 mg in 0.3 mL water, 0.1 mmol) at 0° C. The mixture was stirred at 0° C. for 2 hrs before NaN3 (7.8 mg in 1.0 mL water, 0.12 mmol) was added at 0° C. The mixture was stirred at 0° C. for 1 hour and concentrated. The residue was purified by HPLC (acetonitrile/water) to give T446 as a light yellow solid (23.0 mg, 64%). 1H NMR (400 MHz, CD3OD): δ 8.31 (d, J=8.8 Hz, 1H), 8.10 (m, 2H), 8.00 (m, 1H), 7.90 (d, J=8.8 Hz, 1H), 7.85 (dd, J=8.2, 1.4 Hz, 1H), 7.69 (m, 1H), 7.50 (m, 1H), 7.16 (m, 2H); MS (ESI): 247 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08491869B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-fdc49eb924c74b06ac6c5bb04d5de4c9 |
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| Source note | uspto-grants-2013_07 |
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