Hydrochloric Acid → HCID 59786793, compound

HRID 1256681Notes

Reaction equation

HRID 1256681 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11](=[O:25])[CH2:12][C:13]2[C:18]([O:19][CH3:20])=[CH:17][C:16]([O:21][CH3:22])=[CH:15][C:14]=2[O:23][CH3:24])[CH:5]=1.[Li+].[OH-].Cl>C1COCC1>[CH3:20][O:19][C:18]1[CH:17]=[C:16]([O:21][CH3:22])[CH:15]=[C:14]([O:23][CH3:24])[C:13]=1[CH2:12][C:11]([NH:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:26])=[O:2])=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59786800HCID 59786800, compound

Product 1

HCID 59786793HCID 59786793, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 3-[2-(2,4,6-Trimethoxy-phenyl)-acetylamino]-benzoic acid methyl ester (16) (140 mg, 0.39 mmol) in THF (25.0 mL) at rt and add 1M aqu LiOH (2.0 mL, 2.0 mmol). Stir reaction mixture 40 h at rt. Quench reaction mixture (cooling bath) with 2M aqu. HCl. Extract the mixture with EtOAc (3×), wash the combined organic layer with brine and dry with Na2SO4 to obtain 3-[2-(2,4,6-Trimethoxy-phenyl)-acetylamino]-benzoic acid (17) (134 mg, 99%) as a beige solid. 1H NMR (400 MHz, CD3OD): 3.71 (s, 2H); 3.84 (s, 3H); 3.85 (s, 6H); 6.29 (s, 2H); 7.43 (t, 1H, J=7.8 Hz); 7.76 (d, 1H, J=7.8 Hz); 7.83 (d, 1H, J=8.1 Hz); 8.19 (br.s, 1H).

Workup

  1. customreaction mixture 40 h at rt
  2. customQuench
  3. customreaction mixture (cooling bath) with 2M aqu
  4. extractionExtract the mixture with EtOAc (3×)
  5. washwash the combined organic layer with brine
  6. dry with materialdry with Na2SO4

Sources & evidence

ORD record
ord-25095fd907224c40b72b959cd3fa7ae1
Source dataset
uspto-grants-2013_06
Patent number
US08461207B2

Reaction notes

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