Lithium Hydroxide → HCID 59416009, compound

HRID 2061864Notes

Reaction equation

HRID 2061864 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([I:18])=[CH:15][CH:16]=2)[C:11](=[O:19])[C:10]([C:20]([O:22]CC)=[O:21])=[CH:9]1)[CH2:5][O:6][CH3:7].[OH-].[Li+]>O1CCCC1.O>[CH3:1][O:2][CH2:3][CH:4]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([I:18])=[CH:15][CH:16]=2)[C:11](=[O:19])[C:10]([C:20]([OH:22])=[O:21])=[CH:9]1)[CH2:5][O:6][CH3:7]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59415956HCID 59415956, compound2×

Product 1

HCID 59416009HCID 59416009, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-(1,3-dimethoxypropan-2-yl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (Intermediate 22, 270 mg, 0.60 mmol) was dissolved in tetrahydrofuran (20 mL) and water (5 mL). Lithium hydroxide (56 mg, 2.42 mmol) was added and the mixture was stirred for 10 min at room temperature. The reaction mixture was then refluxed at 80° C. for 1 h. The reaction mixture was concentrated under reduced pressure and water (10 mL) was added. The pH was adjusted to 2 with hydrochloric acid (2N) and the solid that precipitated was collected by filtration and dried to afford 185 mg (75%) of 1-(1,3-dimethoxypropan -2-yl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylic acid.

Workup

  1. temperatureThe reaction mixture was then refluxed at 80° C. for 1 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure and water (10 mL)
  3. additionwas added
  4. customthe solid that precipitated
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-a86ba0cba9ad4aeeae4361c3d7e875b3
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

Loading…