Sulfuric Acid → HCID 178427896, compound
Reaction equation
N([O-])=O.[Na+].[I:5][C:6]1[CH:7]=[C:8]([CH3:13])[C:9](N)=[N:10][CH:11]=1.[OH:14]S(O)(=O)=O.B(O)(O)O.[NH4+].[OH-]>>[I:5][C:6]1[CH:7]=[C:8]([CH3:13])[C:9]([OH:14])=[N:10][CH:11]=1N([O-])=O.[Na+].[I:5][C:6]1[CH:7]=[C:8]([CH3:13])[C:9](N)=[N:10][CH:11]=1.[OH:14]S(O)(=O)=O.B(O)(O)O.[NH4+].[OH-]>>[I:5][C:6]1[CH:7]=[C:8]([CH3:13])[C:9]([OH:14])=[N:10][CH:11]=1Sodium nitrite (0.708 g, 10.25 mmol) was added to a mixture of 5-iodo-3-methyl-pyridin-2-ylamine (2 g, 8.55 mmol) and H2SO4 (12 mL) at 0° C. The reaction mixture was stirred 15 min at 60° C., allowed to cool down, and poured onto crushed ice. Boric acid (1.057 g, 17.09 mmol) was added and the solution was quickly heated to 100° C. The reaction mixture was cooled down and neutralized with a saturated aq. NH4OH solution. The suspension was filtered to afford the crude title product (1.67 g, 7.11 mmol, 83% yield) as a brown solid. tR: 2.85 min (HPLC 1); tR: 0.62 min (LC-MS 2); ESI-MS: 236 [M+H]+ (LC-MS 2).
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