Lithium Hydroxide → 6-(Isoindoline-2-carboxamido)pyridazine-3-carboxylic acid

HRID 624208Notes

Reaction equation

HRID 624208 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[C:10]([NH:12][C:13]1[N:18]=[N:17][C:16]([C:19]([O:21]C)=[O:20])=[CH:15][CH:14]=1)=[O:11].[Li+].[OH-]>CO.C1COCC1.O>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[C:10]([NH:12][C:13]1[N:18]=[N:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=1)=[O:11]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 68753001Methyl 6-(isoindoline-2-carboxamido)pyridazine-3-carboxylate

Product 1

HCID 687492076-(Isoindoline-2-carboxamido)pyridazine-3-carboxylic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-(isoindoline-2-carboxamido)pyridazine-3-carboxylate (3.7 g, 12.4 mmol) in MeOH (40 mL) and THF (40 mL), a solution of LiOH (0.7 g, 29.2 mmol) in water (10 mL) was added at room temperature. The reaction mixture was stirred overnight at room temperature. The reaction mixture was poured into water (100 mL), extracted with EtOAc (2×50 mL) and the aqueous layer was acidified by addition of 2 NHCl to pH 3 to give a precipitate. The precipitate was washed with water and dried in high vacuum to give the title compound.

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. additionthe aqueous layer was acidified by addition of 2 NHCl to pH 3
  3. customto give a precipitate
  4. washThe precipitate was washed with water
  5. customdried in high vacuum

Sources & evidence

ORD record
ord-b297a807e61847b2aeb6e884158c1f3f
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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