Lithium Hydroxide → 4-Acetamido-5-chloro-2-methoxybenzoic acid

HRID 2363383Notes

Reaction equation

HRID 2363383 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([NH:11][C:12](=[O:14])[CH3:13])=[CH:6][C:5]=1[O:15][CH3:16].[Li+].[OH-]>CO>[C:12]([NH:11][C:7]1[C:8]([Cl:10])=[CH:9][C:4]([C:3]([OH:17])=[O:2])=[C:5]([O:15][CH3:16])[CH:6]=1)(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 77721Methyl 4-acetamido-5-chloro-2-methoxybenzoate

Product 1

HCID 109884964-Acetamido-5-chloro-2-methoxybenzoic acidYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Acetylamino-5-chloro-2-methoxy-benzoic acid methyl ester (2.09 g, 8.11 mmol) was dissolved in MeOH (110 ml) and LiOH solution (25.48 mmol in 30 ml, 1:1 MeOH:H2O) added and the solution stirred at room temperature for 6 hours. The solvent was concentrated in vacuo, EtOAc added and the organic phase was washed with 0.5N HCl then extracted with saturated NaHCO3 (2×) . The aqueous phase was acidified with 12N HCl to pH 1 and the resulting precipitate extracted into CH2Cl2. The combined extracts were dried over anhydrous Na2SO4, filtered and evaporated to give the title compound as a white solid (0.933 g, 50% yield). 1H-NMR (500 MHz, CDCl3) δ 2.31 (s, 3H), 4.10 (s, 3H), 7.78-7.92 (br s, 1H), 8.17 (s, 1H), 8.45 (s, 1H). Analytical HPLC 5.62 min.

Workup

  1. concentrationThe solvent was concentrated in vacuo, EtOAc
  2. additionadded
  3. washthe organic phase was washed with 0.5N HCl
  4. extractionthen extracted with saturated NaHCO3 (2×)
  5. extractionthe resulting precipitate extracted into CH2Cl2
  6. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-ccebde9385384ddfac59ad2ad0a8c0b6
Source dataset
uspto-grants-2014_04
Patent number
US08691848B2

Reaction notes

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