Lithium Hydroxide → HCID 59233185, compound

HRID 1925150Notes

Reaction equation

HRID 1925150 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8](C)([C:14](OCC)=O)[C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1.[Li+:20].[OH-]>CO.O>[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH:8]([CH3:14])[C:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.[Li+:20]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59233051HCID 59233051, compound

Product 1

HCID 59233185HCID 59233185, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of diethyl 2-(6-chloropyridazin-3-yl)-2-methylmalonate (19.8 g, 69.1 mmol) and LiOH (3.31 g, 138 mmol) in MeOH:Water (3:1, 200 mL) was stirred at 25° C. for 3 hrs. MeOH was removed from the reaction via rotary evaporation, and the resulting residue was reconstituted in H2O (300 mL). The aqueous mixture was washed with Et2O (3×100 mL) and then lyophilized to dryness to provide lithium 2-(6-chloropyridazin-3-yl)propanoate 48B in quantitative yield. The material was used without further work-up. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.36 (3 H, d, J=7.33 Hz) 3.63 (1 H, q, J=7.24 Hz) 7.71 (2 H, s). ESI-MS:m/z 187.0 (M+H)+.

Workup

  1. customMeOH was removed from the reaction via rotary evaporation
  2. washThe aqueous mixture was washed with Et2O (3×100 mL)

Sources & evidence

ORD record
ord-f5de37a5cf0a4dea941914518b88a4a9
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

Loading…