Methanol → 2-Chloro-5-(cyclopropanecarboxamidomethyl)benzoic acid

HRID 59327Notes

Reaction equation

HRID 59327 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].CO.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:14]([CH:16]2[CH2:18][CH2:17]2)=[O:15])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 89443034Methyl 2-chloro-5-(cyclopropanecarboxamidomethyl)benzoate

Product 1

HCID 715157952-Chloro-5-(cyclopropanecarboxamidomethyl)benzoic acidYield 52.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-chloro-5-(cyclopropanecarboxamidomethyl)benzoate (10.0 g, 30 mmol) in THF: methanol (10:20 mL) was added aqueous solution of NaOH (6.0 g, 140 mmol). The reaction mixture was refluxed for 3-5 h. The reaction mixture was concentrated, diluted with water and acidified with dilute HCl. The reaction mixture was extracted with 10% MeOH:DCM and concentrated to afford 4.0 g of desired product. 1H NMR (300 MHz, DMSO de): δ 0.67 (m, 4H), 1.59 (m, 1H), 4.28 (d, J=6.0 Hz, 2H), 7.37-7.50 (m, 2H), 7.65 (s, 1H), 8.64 (m, 1H), 13.40 (br s, 1H).

Workup

  1. temperatureThe reaction mixture was refluxed for 3-5 h
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with water
  4. extractionThe reaction mixture was extracted with 10% MeOH
  5. concentrationDCM and concentrated

Sources & evidence

ORD record
ord-b918474e5d95435c95b69f4786abf435
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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