Hydrazine hydrate (1:1) → 4-Amino-2-methyl-2,3-dihydropyridazin-3-one

HRID 1842357Notes

Reaction equation

HRID 1842357 reaction equation
Cl[C:2]1[C:3](=[O:11])[N:4]([CH3:10])[N:5]=[CH:6][C:7]=1OC.O.[NH2:13]N>O>[NH2:13][C:2]1[C:3](=[O:11])[N:4]([CH3:10])[N:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27749384-Chloro-5-methoxy-2-methyl-2,3-dihydropyridazin-3-one

Product 1

HCID 131036364-Amino-2-methyl-2,3-dihydropyridazin-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

9.14 g (52 mmoles) of intermediate 4b are placed in mL hydrazine monohydrate. The reaction medium is agitated for 3 h at 80° C. then diluted in 100 mL water and extracted with CH2Cl2 then with AcOEt. After drying over Na2SO4, the organic phases are evaporated and the residue obtained is purified by silica gel flash chromatography (CH2Cl2—AcOEt, gradient 100:0 to 0:100 over 50 min). 4.17 g of intermediate 4c are thus obtained in the form of an orange-like solid (yield 63%). TLC silica 60 F 254 Merck, CH2Cl2—AcOEt: 50:50, Rf=0.16.

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialAfter drying over Na2SO4
  3. customthe organic phases are evaporated
  4. customthe residue obtained
  5. customis purified by silica gel flash chromatography (CH2Cl2—AcOEt, gradient 100:0 to 0:100 over 50 min)

Sources & evidence

ORD record
ord-a7861dec52c14d0bb7c4212acbec0bcd
Source dataset
uspto-grants-2015_02
Patent number
US08946225B2

Reaction notes

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