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

HRID 2068527Notes

Reaction equation

HRID 2068527 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2([C:12]([O:14]CC)=[O:13])[CH2:11][CH2:10]2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Li+]>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2([C:12]([OH:14])=[O:13])[CH2:10][CH2:11]2)=[O:7])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58304106Ethyl 1-[(4-chlorobenzoyl)amino]cyclopropanecarboxylate

Product 1

HCID 583040411-[(4-Chlorobenzoyl)amino]cyclopropanecarboxylic acidYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To ethyl 1-[(4-chlorobenzoyl)amino]cyclopropanecarboxylate (157 g, 0.58 mol) in 1,4-dioxane (2.4 L), add a solution of lithium hydroxide (123.05 g, 2.93 mol) in water (1.2 L). Stir the reaction mixture at ambient temperature for 4 hours and then concentrate it under reduced pressure. Dilute the mixture with water (1 L) and immerse it in an ice water bath. Adjust the pH to approximately 2 with aqueous 5N HCl. Filter the precipitate, wash the cake with water (3×1 L), and dry (50° C., vacuum oven) to give (132 g, 94%) the title compound as a white powder: MS (m/z): 240 (M+1).

Workup

  1. concentrationconcentrate it under reduced pressure
  2. additionDilute the mixture with water (1 L)
  3. filtrationFilter the precipitate
  4. washwash the cake with water (3×1 L)
  5. customdry (50° C., vacuum oven)

Sources & evidence

ORD record
ord-67b0bfc1b5e94bde8e68cd6ac29292a7
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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