Sodium Hydroxide → HCID 178429280, compound

HRID 1735386Notes

Reaction equation

HRID 1735386 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([Br:13])=[CH:8][N:7]=1.[OH-:14].[Na+]>O.S(=O)(=O)(O)O>[Br:13][C:9]1[CH:8]=[N:7][C:6]([OH:14])=[CH:11][C:10]=1[CH3:12]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 8176952-Amino-5-bromo-4-methylpyridineHCID 23668193Sodium Nitrite

Product 1

HCID 178429280HCID 178429280, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Sodium nitrite (5.44 g, 78.8 mmol) in water (14 ml) was added dropwise to 2-amino-5-bromo-4-methylpyridine (12.83 g, 68.6 mmol) in sulphuric acid (20%) (69 ml) at 0-5° C. After 1 h at 0° C. the solution was heated to reflux for 1 h. The solution was basified to pH 10 with sodium hydroxide solution (40%) and cooled to 5° C. and the precipitated product separated by filtration. Recrystallisation from ethanol gave the title compound (5.97 g, 31%) as white needles (m.p.200°-201° C.); δH (D6 -DMSO) 2.17 (3H, s, CH3), 6.40 (1H, s, 3-H), 7.76 (1H, s, 6-H), 11.58 (1H, s, NH): m/z (E.I.) 189 (M+, 100%), 187 (M+, 97%); (Found: M+, 186.9634. C6H6NOBr requires M, 186.9633).

Workup

  1. temperatureto reflux for 1 h
  2. temperaturecooled to 5° C.
  3. customthe precipitated product separated by filtration
  4. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-34753cc809f047bfa703eddf302f46ea
Source dataset
uspto-grants-1996_07
Patent number
US05536745

Reaction notes

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