Hydrochloric Acid → HCID 58728569, compound

HRID 1992225Notes

Reaction equation

HRID 1992225 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][NH:12][C:13]([C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:18]([O:20]C)=[O:19])=[O:14].[Li+].[OH-].Cl>CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][NH:12][C:13]([C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:18]([OH:20])=[O:19])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58728531HCID 58728531, compound

Product 1

HCID 58728569HCID 58728569, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-[({[2,4-bis(methyloxy)phenyl]methyl}amino)carbonyl]-4-chlorobenzoate (600 mg, 1.65 mmol) dissolved in 17 mL CH3OH was treated with 16.5 mL 1N LiOH at ambient temperature for 16 h. The reaction mixture was concentrated to dryness, partitioned between EtOAc and water, the aqueous phase isolated and the pH adjusted to 2 with 6N HCl. The resultant precipitate was cooled in an ice bath with stirring, filtered, and washed with water to give 3-[({[2,4-bis(methyloxy)phenyl]methyl}amino)carbonyl]-4-chlorobenzoic acid (533 mg, 1.52 mmol) as a white crystalline solid. 1H NMR (300 MHz, DMSO-D6) d ppm 8.96 (m, 1H), 8.29 (d, J=2.2 Hz, 1H), 8.00 (dd, J=8.4, 2.3 Hz, 1H), 7.65 (d, J=8.3 Hz, 1H), 7.09 (d, J=8.3 Hz, 1H), 6.55 (d, J=2.3 Hz, 1H), 6.50 (dd, J=8.3, 2.3 Hz, 1H), 4.35 (d, J=5.6 Hz, 1H), 3.79 (s, 3H), 3.73 (s, 3H). LCMS ES+ 349.88, 351.91 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompartitioned between EtOAc and water
  3. customthe aqueous phase isolated
  4. filtrationfiltered
  5. washwashed with water

Sources & evidence

ORD record
ord-8a94292b8ffb41ff8c2f4f40dd27364f
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

Loading…