Hydrochloric Acid → 1-(5-Carboxypentyl)-2-(1-imidazolyl)-3-methylindole hydrochloride

HRID 1903411Notes

Reaction equation

HRID 1903411 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH3:19])=[C:11]1[N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)=[O:4].[OH-].[Na+].[ClH:27]>C(O)C.C(OCC)C>[ClH:27].[C:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH3:19])=[C:11]1[N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)([OH:4])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 132808401-(5-Methoxycarbonylpentyl)-2-(1-imidazolyl)-3-methylindole

Product 1

HCID 202681941-(5-Carboxypentyl)-2-(1-imidazolyl)-3-methylindole hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-(5-methoxycarbonylpentyl)-2-(1-imidazolyl)-3-methylindole (1.80 g) and 30 ml of 3 N NaOH is stirred at room temperature for 1.3 hours. The resulting clear, yellow solution is neutralized to pH 6 with 2 N HCl. The resulting suspension is extracted with ethyl acetate (2×50 ml). The organic extract is washed with a saturated NaCl solution (1×25 ml), dried (MgSO4), filtered, and concentrated in vacuo to give a cream-colored solid. The solid is dissolved in ethanol and the solution treated with 0.6 ml of 6.5 N HCl in ethanol. The solution is diluted with diethyl ether and after standing for several hours the precipitate whch forms is collected by filtration to give 1-(5-carboxypentyl)-2-(1-imidazolyl)-3-methylindole hydrochloride, m.p. 177.5°-180.5° dec.

Workup

  1. extractionThe resulting suspension is extracted with ethyl acetate (2×50 ml)
  2. extractionThe organic extract
  3. washis washed with a saturated NaCl solution (1×25 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a cream-colored solid
  8. waitafter standing for several hours
  9. filtrationthe precipitate whch forms is collected by filtration

Sources & evidence

ORD record
ord-4b7082e2d3bd4083bd37e8f73e14d6e8
Source dataset
uspto-grants-1984_03
Patent number
US04436746

Reaction notes

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