Sodium Hydroxide → 5-Bromo-4,6-dimethylpyridine-2,3-diamine

HRID 1455919Notes

Reaction equation

HRID 1455919 reaction equation
Cl[Sn]Cl.[NH2:4][C:5]1[C:10]([N+:11]([O-])=O)=[C:9]([CH3:14])[C:8]([Br:15])=[C:7]([CH3:16])[N:6]=1.[OH-].[Na+]>Cl>[Br:15][C:8]1[C:9]([CH3:14])=[C:10]([NH2:11])[C:5]([NH2:4])=[N:6][C:7]=1[CH3:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 36499475-Bromo-4,6-dimethyl-3-nitro-2-pyridinylamine

Product 1

HCID 158277935-Bromo-4,6-dimethylpyridine-2,3-diamine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 4.1 g (21.6 mmol) of SnCl2 in 20 ml of concentrated HCl is cooled in an ice bath. 1.32 g (5.4 mmol) of product obtained in Stage B are added gradually. The mixture is heated at 80° C. for 30 minutes. It is allowed to cool and then poured onto crushed ice. The resulting mixture is basified by addition of sodium hydroxide. The precipitate formed is filtered off, washed with water and then dried. 1.06 g of white powder are thus collected. The product is recrystallized from toluene.

Workup

  1. temperatureto cool
  2. additionpoured
  3. customonto crushed ice
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washwashed with water
  7. customdried
  8. custom1.06 g of white powder are thus collected
  9. customThe product is recrystallized from toluene

Sources & evidence

ORD record
ord-25f4173152ea4ea78971f554696359c5
Source dataset
uspto-grants-1998_12
Patent number
US05843947

Reaction notes

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