Hydrochloric Acid → HCID 10269207, compound

HRID 1756405Notes

Reaction equation

HRID 1756405 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]([N+:26]([O-:28])=[O:27])[CH:24]=2)[NH:19][CH:18]=1)[C:9]([O:11]C)=[O:10].Cl>O.CO>[N+:26]([C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH2:16][C:15]1[CH:14]=[CH:13][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[O:5][CH3:4])([O-:28])=[O:27]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 114732633-(2-Methoxy-4-methoxycarboxybenzyl)-5-nitroindole

Product 1

HCID 10269207HCID 10269207, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of lithium hydroxide monohydrate (1.2 g.) in water (20 ml.) was added to a suspension of nitro ester (C) (2.0 g.) in methanol (30 ml.). The mixture was stirred at ambient temperature for 18 hours and then acidified with hydrochloric acid (1N, 50 ml.). The yellow precipitate was isolated by filtration, washed with water, and dried to give 4-(5-nitroindol-3-ylmethyl)-3-methoxybenzoic acid; partial NMR (250 MHz, DMSO-d6): 3.92(s,3H, OMe); 4.12(s,2H, ArCH2); 11.64(br s,1H, NH).

Workup

  1. customThe yellow precipitate was isolated by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-7a43b56c7c8349efa0385a9fa970d758
Source dataset
uspto-grants-1995_08
Patent number
US05440035

Reaction notes

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