Hydrogen Bromide → HCID 86093998, compound

HRID 2262380Notes

Reaction equation

HRID 2262380 reaction equation
N[C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5]([CH3:10])=[CH:4][N:3]=1.[BrH:11].BrBr.N([O-])=O.[Na+].[OH-].[Na+]>O.C(OCC)(=O)C>[Br:11][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5]([CH3:10])=[CH:4][N:3]=1

Participants

8

Reactant 5

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 24408BromineHCID 23668193Sodium Nitrite2×HCID 57674668HCID 57674668, compound

Product 1

HCID 86093998HCID 86093998, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-13.5 °C

Procedure

10.3 g (0.075 mol) of 2-amino-3,4,5-trimethylpyridine was added to 30 mL of 60% HBr. The mixture was cooled to −10 to −17° C. and pre-cooled 36.0 g (0.23 mol) bromine was added dropwise and the mixture was stirred for 20 mins. Pre-cooled (0° C.) NaNO2 solution of 13.5 g (0.19 mol) NaNO2 dissolved in 20 mL water was added dropwise into the reaction mixture at −10° C.˜−17° C. After addition, the reaction was stirred for one hour. Ice-cooled 25% NaOH solution was added slowly until the solution became basic. 200 mL of ethyl acetate was added to the mixture to extract the organic phase. The organic phase solvent was evaporated and the residue was distilled under vacuum. ˜13.1 g (87% yield) of the desired product was obtained which was confirmed by GC/MS.

Workup

  1. additionwas added dropwise
  2. additionwas added dropwise into the reaction mixture at −10° C.˜−17° C
  3. additionAfter addition
  4. stirringthe reaction was stirred for one hour
  5. additionwas added slowly until the solution
  6. extractionto extract the organic phase
  7. customThe organic phase solvent was evaporated
  8. distillationthe residue was distilled under vacuum

Sources & evidence

ORD record
ord-8f4e642b8ca04586b9b8a4a744f58825
Source dataset
uspto-grants-2010_12
Patent number
US07851072B2

Reaction notes

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