Sodium Hydroxide → 1-(4-Cyclopropoxybenzamido)cyclopropanecarboxylic acid

HRID 2068550Notes

Reaction equation

HRID 2068550 reaction equation
[CH:1]1([O:4][C:5]2[CH:21]=[CH:20][C:8]([C:9]([NH:11][C:12]3([C:15]([O:17]CC)=[O:16])[CH2:14][CH2:13]3)=[O:10])=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([O:4][C:5]2[CH:21]=[CH:20][C:8]([C:9]([NH:11][C:12]3([C:15]([OH:17])=[O:16])[CH2:13][CH2:14]3)=[O:10])=[CH:7][CH:6]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67234427Ethyl 1-(4-cyclopropoxybenzamido)cyclopropanecarboxylate

Product 1

HCID 672344531-(4-Cyclopropoxybenzamido)cyclopropanecarboxylic acidYield 1,766%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of ethyl 1-(4-cyclopropoxybenzamido)cyclopropanecarboxylate (33.7 g, 6.48 mmol) in ethanol (380 mL), add sodium hydroxide (174.7 mL, 174.7 mmol) and stir the mixture at 65° C. for 3 hours. Cool the material to ambient temperature and concentrate under reduced pressure to remove the ethanol. Acidify the residue with 10% NaHSO4. Filter the resulting solid and wash with water (3×) and diethyl ether (2×). Dry the material in a vacuum oven to give the title compound (29.9 g, 98%) as a white solid: MS (m/z): 262 (M+1).

Workup

  1. temperatureCool the material to ambient temperature
  2. concentrationconcentrate under reduced pressure
  3. customto remove the ethanol
  4. filtrationFilter the resulting solid
  5. washwash with water (3×) and diethyl ether (2×)
  6. customDry the material in a vacuum oven

Sources & evidence

ORD record
ord-131bf4a57940420d8e6638ba134154f9
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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