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

HRID 1633128Notes

Reaction equation

HRID 1633128 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 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 1-(4-carboxybenzyl)-3-methyl-2-(3-pyridyl)indole, m.p. 273°-275°.

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-cc53fcda6cce4a29bb783748cbf1b483
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

Loading…