Sodium Azide → HCID 58362457, compound

HRID 2361481Notes

Reaction equation

HRID 2361481 reaction equation
Cl.Cl.[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.N([O-])=O.[Na+].[N-:24]=[N+:25]=[N-].[Na+]>Cl>[N:17]([C:16]1[CH:18]=[CH:19][C:13]([C:4]2[CH:5]=[CH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:3]=2)=[CH:14][CH:15]=1)=[N+:24]=[N-:25]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 66700259HCID 66700259, compound

Product 1

HCID 58362457HCID 58362457, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

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+).

Workup

  1. additionwas added at 0° C
  2. concentrationconcentrated
  3. customThe residue was purified by HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-e4b5911aca004cbbbbd3678cae46cec5
Source dataset
uspto-grants-2014_04
Patent number
US08691187B2

Reaction notes

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