Sodium Hydroxide → 2-Amino-3-bromo-5-methylpyridine

HRID 1828759Notes

Reaction equation

HRID 1828759 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[Br:9]Br.[OH-].[Na+]>C(O)(=O)C.CCOCC>[NH2:1][C:2]1[C:7]([Br:9])=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 153482-Amino-5-methylpyridineHCID 24408Bromine

Product 1

HCID 5193802-Amino-3-bromo-5-methylpyridine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-amino-5-picoline (5 g) in acetic acid (40 mL) at r.t. was added bromine (2.6 mL) slowly. After 1 h, the acid was neutralized by the careful addition of sodium hydroxide (10 N) at 0° C. The resulting orange precipitate was dissolved in ether and washed successively with saturated potassium carbonate, saturated Na2S2O3 and brine, dried and concentrated. Flash chromatography (eluting with hexane/ethyl acetate, 3:2 v/v) of the residual solid provided the title compound as a pale yellow solid (7.1 g).

Workup

  1. washwashed successively with saturated potassium carbonate, saturated Na2S2O3 and brine
  2. customdried
  3. concentrationconcentrated
  4. washFlash chromatography (eluting with hexane/ethyl acetate, 3:2 v/v) of the residual solid

Sources & evidence

ORD record
ord-e1a6d35cdc6047258ddf4380e08ec091
Source dataset
uspto-grants-2006_06
Patent number
US07060715B2

Reaction notes

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