Water → HCID 89876179, compound

HRID 2169758Notes

Reaction equation

HRID 2169758 reaction equation
[OH-:1].[Na+].O.[Cl:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14]2[C:15](=[O:31])[N:16]([CH3:30])[N:17]=[CH:18][C:19]=2N2C3C(=CC=CC=3)C(Cl)=N2)[N:6]=1>CO>[Cl:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([CH:14]2[C:19](=[O:1])[CH:18]=[N:17][N:16]([CH3:30])[C:15]2=[O:31])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 89876371HCID 89876371, compound

Product 1

HCID 89876179HCID 89876179, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A 1:1 w/w 32% NaOH:water mixture (8 g total) is added to 4,5-bis(3-chloroindazol-1-yl)-2-methyl-pyridazin-3-one (768 mg, 1.87 mmol) in methanol (30 mL) and then the mixture heated at 80° C. for 20 minutes. The mixture is allowed to cool to room temperature then concentrated in vacuo. Dichloromethane (50 mL) and water (50 mL) are added to the residue and the organic layer removed. The aqueous layer is acidified to pH 1 with conc. HCl. then extracted with dichloromethane (40 mL×2). The combined organic extracts are passed through a phase separator cartridge and concentrated in vacuo to give the title compound as a white solid (490 mg). 1H nmr (DMSO-d6) δ (ppm) 7.93 (1 H, s) 7.71-7.79 (1 H, m) 7.45-7.54 (1 H, m) 7.26-7.38 (2 H, m) 3.66 (3 H, s). Some other dione products prepared analogously were triturated with ethyl acetate or ether.

Workup

  1. temperatureto cool to room temperature
  2. concentrationthen concentrated in vacuo
  3. additionDichloromethane (50 mL) and water (50 mL) are added to the residue
  4. customthe organic layer removed
  5. extractionthen extracted with dichloromethane (40 mL×2)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb25736094304d99bfb440c3aebd693d
Source dataset
uspto-grants-2015_06
Patent number
US09049864B2

Reaction notes

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