6-Amino-3-chloropyridazine → HCID 68456032, compound

HRID 2356242Notes

Reaction equation

HRID 2356242 reaction equation
[Na].[CH:2]1([CH2:5][OH:6])[CH2:4][CH2:3]1.Cl[C:8]1[N:13]=[N:12][C:11]([NH2:14])=[CH:10][CH:9]=1>O>[CH:2]1([CH2:5][O:6][C:8]2[N:13]=[N:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 216436-Amino-3-chloropyridazineHCID 75644CyclopropanemethanolHCID 5360545Sodium2×

Product 1

HCID 68456032HCID 68456032, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium (127 mg) was added to a stirred cyclopropylmethanol (5 g). After the sodium had dissolved, 6-chloropyridazin-3-amine (0.648 g) was added and the mixture was heated to 170° in a glass pressure vessel with magnetic stirring for 23 h. The cooled reaction mixture was diluted with water and extracted with chloroform (3×50 mL). The combined extracts were dried (sodium sulfate) and evaporated to afford crude 6-cyclopropylmethoxypyridazin-3-amine (716 mg). 1H n.m.r. (CDCl3) δ 0.27-0.38, m, 2H; 0.52-0.66, m, 2H; 1.18-1.38, m, 1H; 4.18, d, 2H; 4.47 broad s, 2H; 7.78, AB q, 2H.

Workup

  1. temperaturethe mixture was heated to 170° in a glass pressure vessel
  2. customThe cooled reaction mixture
  3. extractionextracted with chloroform (3×50 mL)
  4. dry with materialThe combined extracts were dried (sodium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-2d66cb2d70ee405da44df111a945e133
Source dataset
uspto-grants-2010_07
Patent number
US07759349B2

Reaction notes

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