Sulfuric Acid → HCID 178515817, compound

HRID 1486949Notes

Reaction equation

HRID 1486949 reaction equation
N([O-])=O.[Na+].[Br:5][C:6]1[CH:7]=[CH:8][C:9](N)=[N:10][C:11]=1[F:12].S(=O)(=O)(O)[OH:15]>O>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([OH:15])=[N:10][C:11]=1[F:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 534184365-Bromo-6-fluoropyridin-2-amine

Product 1

HCID 178515817HCID 178515817, compoundYield 925.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (21.67 g, 314.13 mmol) in water (150 mL) was added dropwise to a stirred mixture of 5-bromo-6-fluoropyridin-2-amine (50 g, 261.78 mmol) and sulphuric acid (1.2 mL, 22.51 mmol) in water (750 mL) at 0-5° C. The resulting suspension was stirred for 48 h at ambient temperature then the precipitate collected by filtration, washed with water (200 mL) and dried under vacuum to afford the desired material (40.0 g, 80%) as a pale yellow solid, which was used without further purification. NMR Spectrum: 1H NMR (300 MHz, DMSO-d6) δ 6.55 (1H, d), 8.00 (1H, t), 11.71 (1H, bs). Mass Spectrum: m/z (ES+)[M+H]+=192.

Workup

  1. filtrationthe precipitate collected by filtration
  2. washwashed with water (200 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-bbaf0ebd218145c4bbeb65d1bd7636ba
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

Loading…