Lithium Hydroxide → HCID 59406714, compound

HRID 383632Notes

Reaction equation

HRID 383632 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH:28]=[CH:29][CH:30]=1)[CH2:10][N:11]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][CH:19]=2)=[N:12]1)=[O:5])[CH3:2].[OH-].[Li+]>O1CCCC1.O>[CH2:1]([O:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH:28]=[CH:29][CH:30]=1)[CH2:10][N:11]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]([C:18]2[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:26][CH:27]=2)=[N:12]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59406794HCID 59406794, compound

Product 1

HCID 59406714HCID 59406714, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

42 g (22 mmol) of methyl 4-[1-(3-ethoxycarbonylaminobenzyl)-6-oxo-1,6-dihydropyridazin-3-yl]benzoate (contaminated with triphenylphosphine oxide) are dissolved in 300 ml of tetrahydrofuran and 30 ml of water, 1.6 g (66 mmol) of lithium hydroxide are added, and the mixture is stirred at room temperature for 15 h. The reaction mixture is evaporated. The residue is dissolved in 400 ml of water and 200 ml of ethyl acetate, the organic phase is separated off, and the aqueous phase is extracted with 2×200 ml of ethyl acetate. The organic phase is discarded, conc. HCl is added to the aqueous phase to pH 4-5. During this operation, a precipitate deposits, which is filtered off with suction, washed with water and dried.

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionThe residue is dissolved in 400 ml of water
  3. custom200 ml of ethyl acetate, the organic phase is separated off
  4. extractionthe aqueous phase is extracted with 2×200 ml of ethyl acetate
  5. additionconc. HCl is added to the aqueous phase to pH 4-5
  6. filtrationDuring this operation, a precipitate deposits, which is filtered off with suction
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-d2a94eba25b4427f90fefba82208466f
Source dataset
uspto-grants-2013_02
Patent number
US08367668B2

Reaction notes

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