Potassium Hydroxide → alpha-[[(2,4,6-Trimethoxyphenyl)amino]carbonyl]benzene acetic acid

HRID 1756979Notes

Reaction equation

HRID 1756979 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:29])[CH:7]([C:14]([NH:16][C:17]1[C:22]([O:23][CH3:24])=[CH:21][C:20]([O:25][CH3:26])=[CH:19][C:18]=1[O:27][CH3:28])=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C>C(O)C.O>[CH3:28][O:27][C:18]1[CH:19]=[C:20]([O:25][CH3:26])[CH:21]=[C:22]([O:23][CH3:24])[C:17]=1[NH:16][C:14]([CH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:6]([OH:29])=[O:5])=[O:15]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 10690735alpha-[[(2,4,6-Trimethoxyphenyl)amino]carbonyl] benzene acetic acid ethyl ester

Product 1

HCID 10665192alpha-[[(2,4,6-Trimethoxyphenyl)amino]carbonyl]benzene acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of KOH (10.70 g, 0.191 mol) in absolute ethanol (1.1 L) was added α-[[(2,4,6-trimethoxyphenyl)amino]carbonyl] benzene acetic acid ethyl ester (55.28 g, 0.1480 mol), and the mixture was stirred for 41 hours. The resulting suspension was diluted with H2O (~900 mL) and rotoevaporated to remove ethanol. The solution was washed (ethyl acetate) and acidified with dropwise addition of 1M HCl (265 mL). The resulting precipitate was filtered off, washed (H2O), and dried in vacuo to give an off-white solid; yield 48.4 g (100%); 111°-113° C. (gas evolution).

Workup

  1. customto remove ethanol
  2. washThe solution was washed (ethyl acetate)
  3. additionacidified with dropwise addition of 1M HCl (265 mL)
  4. filtrationThe resulting precipitate was filtered off
  5. washwashed (H2O)
  6. customdried in vacuo
  7. customto give an off-white solid
  8. custom111°-113° C. (gas evolution)

Sources & evidence

ORD record
ord-4f82e0a201d247a48662a4833a625b1b
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

Loading…