Lithium Hydroxide → 1-[(4-Ethoxybenzoyl)amino]cyclopropanecarboxylic acid

HRID 2068551Notes

Reaction equation

HRID 2068551 reaction equation
[CH2:1]([O:3][C:4]1[CH:20]=[CH:19][C:7]([C:8]([NH:10][C:11]2([C:14]([O:16]CC)=[O:15])[CH2:13][CH2:12]2)=[O:9])=[CH:6][CH:5]=1)[CH3:2].[OH-].[Li+]>O1CCOCC1.O>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][C:11]2([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]2)=[O:9])=[CH:19][CH:20]=1)[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58304093Ethyl 1-[(4-ethoxybenzoyl)amino]cyclopropanecarboxylate

Product 1

HCID 583041121-[(4-Ethoxybenzoyl)amino]cyclopropanecarboxylic acidYield 73.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Dissolve ethyl 1-[(4-ethoxybenzoyl)amino]cyclopropanecarboxylate (4.25 g, 15.33 mmol) in 1,4-dioxane (60 mL) and add lithium hydroxide (LiOH) (3.22 g, 76.63 mmol) dissolved in water (30 mL). Stir the reaction for approximately 16 hours at ambient temperature. Concentrate the mixture under reduced pressure, add water, acidify with 5N HCl, and collect the precipitate by filtration to give the title compound (2.8 g, 73%) as a white solid: MS (m/z): 248 (M+1).

Workup

  1. customthe reaction for approximately 16 hours at ambient temperature
  2. concentrationConcentrate the mixture under reduced pressure
  3. additionadd water
  4. customcollect the precipitate
  5. filtrationby filtration

Sources & evidence

ORD record
ord-11393c99d8094dba931f8a16b0bc4940
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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