Methyl iodide → 6-Amino-2-methyl-2,3-dihydropyridazin-3-one

HRID 873841Notes

Reaction equation

HRID 873841 reaction equation
[NH2:1][C:2]1[N:7]=[N:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:11]I>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH3:11])[N:7]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178507783HCID 178507783, compound

Product 1

HCID 157119126-Amino-2-methyl-2,3-dihydropyridazin-3-oneYield 24%

Conditions

Temperature
85 °C

Procedure

A mixture of 6-aminopyridazin-3-ol (2 g, 18.00 mmol), NaOH (0.720 g, 18.00 mmol) and MeI (1.126 mL, 18.00 mmol) was stirred for 2.5 hr at 85° C. under Ar. The reaction mixture was concentrated. The crude material was purified by silica gel column chromatography (NH3 1%/CH2Cl2/MeOH 4-7%) to afford the title product (538 mg, 4.30 mmol, 24% yield) as a yellow solid. tR: 0.25 min (LC-MS 2); ESI-MS: 126 [M+H]+ (LC-MS 2); Rf=0.36 (CH2Cl2/MeOH 9:1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe crude material was purified by silica gel column chromatography (NH3 1%/CH2Cl2/MeOH 4-7%)

Sources & evidence

ORD record
ord-d761cc73a5ee4bb398f5b00ebedd3680
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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