Sodium Hydroxide → 3-Bromo-5-chloropyridin-2-amine

HRID 2414451Notes

Reaction equation

HRID 2414451 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[Br:9]Br.[OH-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[C:7]([Br:9])=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 661742-Amino-5-chloropyridine

Product 1

HCID 27639713-Bromo-5-chloropyridin-2-amine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-5-chloropyridine (10 g) in acetic acid (75 mL) at r.t. was added bromine (2.6 mL) slowly. After 30 min, the acid was neutralized by the careful addition of sodium hydroxide (10 N) at 0° C. The resulting orange precipitate was dissolved in ethyl acetate and washed successively with saturated potassium carbonate, saturated Na2S2O3 and brine, dried and concentrated. Flash chromatography (eluting with hexane/ethyl acetate, 3:1 v/v) of the residual solid provided the title compound as a pale yellow solid (14.8 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, 3:1 v/v) of the residual solid

Sources & evidence

ORD record
ord-f871662c3db74f33a50e63342cde094e
Source dataset
uspto-grants-2004_11
Patent number
US06812346B2

Reaction notes

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