Hydrochloric Acid → HCID 20400801, compound

HRID 1980854Notes

Reaction equation

HRID 1980854 reaction equation
C([C:3]1[CH:24]=[CH:23][C:6]([CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:5][CH:4]=1)#N.Cl.[C:26](=[O:29])(O)[O-:27].[Na+]>C(O)(=O)C>[C:26]([C:3]1[CH:24]=[CH:23][C:6]([CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:5][CH:4]=1)([OH:27])=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20400831HCID 20400831, compound

Product 1

HCID 20400801HCID 20400801, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-(4-cyanobenzyl)-2-(3-pyridyl)indole (5.8 g) in 100 ml of a 1:1 mixture of 20% aqueous hydrochloric acid and glacial acetic acid is heated at reflux for 20 hours. After cooling, the solution is poured into ice water (100 ml) and the pH is adjusted to 4.5-5 with saturated sodium bicarbonate solution. The resulting precipitate is extracted with ethyl acetate, the ethyl acetate extract is washed with water and evaporated to dryness to give 3-(4-carboxybenzyl)-2-(3-pyridyl)indole.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 20 hours
  3. temperatureAfter cooling
  4. extractionThe resulting precipitate is extracted with ethyl acetate
  5. extractionthe ethyl acetate extract
  6. washis washed with water
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-3fcb158e3f1a4688b7ddc5de0901584c
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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