Hydrochloric Acid → 3-Bromo-6-chloro-2-methylpyridine

HRID 2224352Notes

Reaction equation

HRID 2224352 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](N)=[N:6][C:7]=1[CH3:8].N([O-])=O.[Na+].[OH-].[Na+].[ClH:16]>>[Br:1][C:2]1[C:7]([CH3:8])=[N:6][C:5]([Cl:16])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1706782-Pyridinamine, 5-bromo-6-methyl-HCID 23668193Sodium Nitrite

Product 1

HCID 148666743-Bromo-6-chloro-2-methylpyridineYield 28%

Conditions

Temperature
0 °C

Procedure

To a solution of 5-bromo-6-methyl-pyridin-2-ylamine (2.0 g, 10.6 mmol) in concentrated HCl (10 mL) was added NaNO2 (1.1 g, 15.9 mmol) at room temperature. The reaction was stirred for 2 hours, then cooled to 0° C., made basic with NaOH and extracted with Et2O. The Et2O layer was dried (MgSO4) and concentrated in vacuo to give 55A (0.63 g, 28%). HPLC Rt=2.29 min.

Workup

  1. extractionextracted with Et2O
  2. dry with materialThe Et2O layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4388ad20ba324f45a0340d8f70556ae0
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

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