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

HRID 611503Notes

Reaction equation

HRID 611503 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-e1f115d484ba47c5998409c866186452
Source dataset
uspto-grants-1999_12
Patent number
US06001843

Reaction notes

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