Sodium Hydroxide → Pyridazine, 3-amino-4,6-dimethyl-

HRID 452469Notes

Reaction equation

HRID 452469 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH3:20])[C:5]2[N:6](C=[N+](CC(=O)C3C=CC=CC=3)[N:10]=2)[N:7]=1.[OH-].[Na+]>>[CH3:20][C:4]1[CH:3]=[C:2]([CH3:1])[N:7]=[N:6][C:5]=1[NH2:10]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 178424061HCID 178424061, compound

Product 1

HCID 205057Pyridazine, 3-amino-4,6-dimethyl-Yield 93%

Procedure

A solution of alkylated salt 2 (2.58 g, 9.65 mmol) in 20% aqueous NaOH solution (29.0 mmol) was heated at reflux for 16 h. The crude reaction mixture was evaporated to dryness and purified by silica gel column chromatography (CHCl3/MeOH, 10:1 (v/v), as eluent), to yield 3 (1.1 g, 93%) as a pale, brown powder; mp: 123-126° C. 1H NMR (CDCl3, 300 MHz) δ: 2.13 (s, 3H), 2.50 (s, 3H), 6.93 (s, 1H). Mass Spectrum: CI, m/z 124 (M+1).

Workup

  1. temperatureat reflux for 16 h
  2. customThe crude reaction mixture
  3. customwas evaporated to dryness
  4. custompurified by silica gel column chromatography (CHCl3/MeOH, 10:1 (v/v), as eluent)

Sources & evidence

ORD record
ord-c4bbc46cdd2e4960a06512b520a8cebf
Source dataset
uspto-grants-2013_07
Patent number
US08492379B2

Reaction notes

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