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Lithium hydroxide, monohydrate → 3-Methoxy-4-[1-methyl-5-[2-(pentylcarbamoyl)propyl]indol-3-ylmethyl]benzoic acid

HRID 330179
Notes
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Reaction equation

HRID 330179 reaction equation
O.[OH-].[Li+].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH2:26][CH:27]([C:29](=[O:36])[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH3:28])[CH:24]=2)[N:19]([CH3:37])[CH:18]=1)[C:9]([O:11]C)=[O:10]>O.CO.O1CCCC1>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH2:26][CH:27]([C:29](=[O:36])[NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH3:28])[CH:24]=2)[N:19]([CH3:37])[CH:18]=1)[C:9]([OH:11])=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 14882559Methyl 3-methoxy-4-[1-methyl-5-[2-(pentylcarbamoyl)propyl]indol-3-ylmethyl]benzoate

Product 1

HCID 198706133-Methoxy-4-[1-methyl-5-[2-(pentylcarbamoyl)propyl]indol-3-ylmethyl]benzoic acidYield 99.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent
HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (0.29 g) in water (5 ml) was added to a solution of methyl 3-methoxy-4-[1-methyl-5-[2-(pentylcarbamoyl)propyl]indol-3-ylmethyl]benzoate (0.65 g) in methanol (25 ml) and tetrahydrofuran (5 ml). The mixture was stirred under an atmosphere of nitrogen for 48 hr, and the solvents evaporated. The residue was taken up in water (5 ml), acidified with 1M hydrochloric acid (10 ml), and the precipitate which formed isolated by filtration to give the title compound (0.63 g, 94%) as a white powder; mp 85°-95°.

Workup

  1. customthe solvents evaporated
  2. customthe precipitate which formed
  3. customisolated by filtration

Sources & evidence

ORD record
ord-78e0068d84ab423bbedc0145bf8d41aa
Source dataset
uspto-grants-1990_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04894386

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes