Hydrochloric Acid → 1-(4-Carboxybenzyl)-3-methyl-2-(3-pyridyl)indole

HRID 1462624Notes

Reaction equation

HRID 1462624 reaction equation
C([C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH3:17])=[C:9]2[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:5][CH:4]=1)#N.Cl.[C:27](=[O:30])(O)[O-:28].[Na+]>C(O)(=O)C>[C:27]([C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH3:17])=[C:9]2[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:5][CH:4]=1)([OH:28])=[O:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 155913804-(3-methyl-2-pyridin-3-yl-1H-indol-1-ylmethyl)-benzonitrile

Product 1

HCID 155913791-(4-Carboxybenzyl)-3-methyl-2-(3-pyridyl)indole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-(4-cyanobenzyl)-3-methyl-2-(3-pyridyl)-indole (5.8 g) in 100 ml of a 1:1 mixture of 20% aqueous hydrochloric acid and glacial acetic acid was heated at reflux for 20 hours. After cooling, the solution was poured into ice water (100 ml) and the pH was adjusted to 4.5-5 with saturated sodium bicarbonate solution. The resulting precipitate was extracted with ethyl acetate, the ethyl acetate extract was washed with water and evaporated to dryness to give 1-(4-carboxybenzyl)-3-methyl-2-(3-pyridyl)indole, m.p. 273°-5°.

Workup

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

Sources & evidence

ORD record
ord-3a6557add24440b6b68fa17778bf336f
Source dataset
uspto-grants-1984_07
Patent number
US04460777

Reaction notes

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