Sodium Hydroxide → HCID 70575775, compound

HRID 1680481Notes

Reaction equation

HRID 1680481 reaction equation
C([O:3][C:4]([C:6]1[CH:27]=[CH:26][C:9]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH2:20][C:21]3[NH:22][CH:23]=[CH:24][N:25]=3)=[CH:12]2)=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+]>C(O)C.O>[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]([CH2:20][C:21]3[NH:25][CH:24]=[CH:23][N:22]=3)=[CH:12]2)=[CH:26][CH:27]=1)([OH:5])=[O:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70577379HCID 70577379, compound

Product 1

HCID 70575775HCID 70575775, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-(4-Ethoxycarbonylbenzyl)-3-(1-imidazolylmethyl)indole (1.53 g) was dissolved in ethanol (25 ml) and a solution of sodium hydroxide (0.2 g) in water (5 ml) was added. The solution was heated under reflux for 2 hours and then evaporated. The residue was taken up in water and the solution was just acidified with acetic acid. A gummy precipitate was formed which solidified on scratching. The solid was filtered off, washed with water and crystallised from ethanol to give 1-(4-carboxybenzyl)-3-(1-imidazolylmethyl)indole (0.76 g), m.p. 234°-235° C. Found: C, 72.32; H, 4.96; N, 12.67. C20H17N3O2 requires: C, 72.49; H, 5.17; N, 12.68.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 2 hours
  3. customevaporated
  4. customA gummy precipitate was formed which
  5. filtrationThe solid was filtered off
  6. washwashed with water
  7. customcrystallised from ethanol

Sources & evidence

ORD record
ord-d28a692690fb43c099495bab91a1716a
Source dataset
uspto-grants-1981_06
Patent number
US04273782

Reaction notes

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