Lithium hydroxide, monohydrate → 1-Ethyl-5-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-1H-indole-2-carboxylic acid

HRID 489990Notes

Reaction equation

HRID 489990 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:34][CH3:35])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([NH:15][C:16]([C:18]1[C:19]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:17])=[CH:10][CH:9]=2)=[O:5])C.O.[OH-].[Li+]>CO.O>[CH2:34]([N:7]1[C:8]2[C:13](=[CH:12][C:11]([NH:15][C:16]([C:18]3[C:19]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:26][CH:25]=4)=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:17])=[CH:10][CH:9]=2)[CH:14]=[C:6]1[C:4]([OH:5])=[O:3])[CH3:35]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 12148798ethyl 1-ethyl-5-({2-[4-(trifluoromethyl)phenyl]benzene}amido)-1H-indole-2-carboxylate

Product 1

HCID 121487951-Ethyl-5-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

1-Ethyl-5-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino]-1H-indole-2-carboxylic acid ethyl ester (4.5 g, 9.37 mmol) was added to MeOH/H2O (110 mL, 10/1). Lithium hydroxide monohydrate (1.5 g, 35.7 mmol) was added to the above mixture. The mixture which resulted was heated to reflux overnight. The solvent was removed under reduced pressure and the residue was dissolved in H2O (500 mL). The solution was acidified with 6N HCl to pH 2. The solid was collected by filtration and dried under vacuum (4.0 g, 94.5%).

Workup

  1. customThe mixture which resulted
  2. temperaturewas heated
  3. temperatureto reflux overnight
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe residue was dissolved in H2O (500 mL)
  6. filtrationThe solid was collected by filtration
  7. customdried under vacuum (4.0 g, 94.5%)

Sources & evidence

ORD record
ord-c7205a9424ce4f5b82848f856297293b
Source dataset
uspto-grants-2005_12
Patent number
US06979692B2

Reaction notes

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