Hydrochloric Acid → HCID 10269207, compound

HRID 275160Notes

Reaction equation

HRID 275160 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-bc3851a7729b42639cf942b3daaa33a8
Source dataset
uspto-grants-1995_02
Patent number
US05391758

Reaction notes

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