Water → 3-Oxo-2,3,-dihydropyridazin-6-yl-propionic acid

HRID 987907Notes

Reaction equation

HRID 987907 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11]CC)=[O:10])=[N:4][NH:3]1.[Li+].[OH-].O>C1COCC1>[O:1]=[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([OH:11])=[O:10])=[N:4][NH:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 131724097Ethyl (3-oxo-2,3,-dihydropyridazin-6-yl)-propionate

Product 1

HCID 688965403-Oxo-2,3,-dihydropyridazin-6-yl-propionic acidYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Ethyl (3-oxo-2,3,-dihydropyridazin-6-yl)-propionate (3.00 mmol, 589 mg) in THF was added LiOH (2M, aqueous) (7.50 mL). The solution was stirred at rt. for 15 minutes, additional water (25 mL) was added and the THF removed in vacuo. The pH of the aqueous phase was adjusted to 3.0 by addition of HCl (2M, aqueous) and the solid material filtered off and washed with water (2×3 mL). The solid was dried in vacuo to yield the desired product (461 mg, 91.4%) as a colorless powder. 1H NMR (CDCl3): δ 11.62 (s br, 1H, NH), 7.18 (d, J=9.7 Hz, 1H, arom.), 7.88 (d, J=9.7 Hz, 1H, arom.), 4.11 (q, J=7.1 Hz, 2H, CH2), 2.90 (t, J=7.0 Hz, 2H, CH2), 2.64 (t, J=7.0 Hz, 2H, CH2), 1.25 (t, J=7.1 Hz, 3H, CH3). FAB+ MS: 169.0611 (M+H+, calc. for C9H12N2O3+H+ 169.0613).

Workup

  1. customthe THF removed in vacuo
  2. additionThe pH of the aqueous phase was adjusted to 3.0 by addition of HCl (2M, aqueous)
  3. filtrationthe solid material filtered off
  4. washwashed with water (2×3 mL)
  5. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-21dd1555815b4d6498b699125031aefa
Source dataset
uspto-grants-2003_10
Patent number
US06632919B1

Reaction notes

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