Sodium Hydroxide → 3-Bromo-2,6-dimethyl-4-pyridinamine

HRID 400573

Reaction equation

HRID 400573 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[Br:10]Br.[OH-].[Na+]>C(O)(=O)C>[NH2:8][C:6]1[CH:5]=[C:4]([CH3:9])[N:3]=[C:2]([CH3:1])[C:7]=1[Br:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 770474-Amino-2,6-dimethylpyridine

Product 1

HCID 105122623-Bromo-2,6-dimethyl-4-pyridinamineYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 2,6-dimethylpyridin-4-ylamine (2.00 g, 16.4 mmol) in 5 mL of acetic acid was treated dropwise with a solution of bromine (0.84 mL, 16.3 mmol) in 2 mL of acetic acid at room temperature in a water bath over a period of 10 minutes. After I hour, the resulting slurry was treated with 40 mL of 20% sodium hydroxide solution and extracted with three 100 mL portions of dichloromethane (CH2Cl2). The combined extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting solid (starting material-desired product-dibromo byproduct (1:3:1)) was dissolved in 100 mL of hot hexanes and hot filtered to remove the insoluble starting material. The filtrate was allowed to cool to room temperature, which gave the title product as fine white needles (1.30 g, 40% yield).

Workup

  1. extractionextracted with three 100 mL portions of dichloromethane (CH2Cl2)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting solid (starting material-desired product-dibromo byproduct (1:3:1)) was dissolved in 100 mL of hot hexanes
  6. filtrationhot filtered
  7. customto remove the

Sources & evidence

ORD record
ord-db834648189a4724bd11503d9cc4ca6c
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Linked notes

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