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

HRID 267936

Reaction equation

HRID 267936 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[CH:4][N:3]=1.O.O.O.C([O-])(=O)C.[Na+].[Br:17]Br.[OH-].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[C:7]([Br:17])=[N:6][C:5]([CH3:8])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 3132155-Methylpyrazin-2-amineHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 98990432-Amino-3-bromo-5-methylpyrazine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Conditions

Temperature
20 °C

Procedure

To acetic acid (1500 ml.), 2-amino-5-methylpyrazine (1 mole) and 326.5 g. sodium acetate trihydrate are slowly added 1.1 mole bromine in 180 ml. acetic acid at 2° C. in the absence of light. The mixture is stirred about 15 hours at 20° C., stripped of acetic acid in vacuo, poured into ice, made alkaline with sodium hydroxide, filtered, the residue extracted with ether, the extract stripped and the 2-amino-3-bromo-5-methylpyrazine crystallized from a suitable solvent.

Workup

  1. customat 2° C.
  2. additionpoured into ice
  3. filtrationfiltered
  4. extractionthe residue extracted with ether
  5. customthe 2-amino-3-bromo-5-methylpyrazine crystallized from a suitable solvent

Sources & evidence

ORD record
ord-1bf49bce1db74c0fae2fb1376987c77a
Source dataset
uspto-grants-1976_03
Patent number
US03946009

Linked notes

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