Sodium Hydroxide → 1-[2-(4-Carboxyphenoxy)ethyl]-2-(3-pyridyl)-3-methylindole

HRID 1633134Notes

Reaction equation

HRID 1633134 reaction equation
C([O:3][C:4]([C:6]1[CH:30]=[CH:29][C:9]([O:10][CH2:11][CH2:12][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH3:22])=[C:14]2[C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Na+]>Cl>[C:4]([C:6]1[CH:30]=[CH:29][C:9]([O:10][CH2:11][CH2:12][N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH3:22])=[C:14]2[C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[CH:8][CH:7]=1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 133621101-[2-(4-Ethoxycarbonylphenoxy)ethyl]-2-(3-pyridyl)-3-methylindole

Product 1

HCID 133620911-[2-(4-Carboxyphenoxy)ethyl]-2-(3-pyridyl)-3-methylindole

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 4.7 g of 1-[2-(4-ethoxycarbonylphenoxy)ethyl]-2-(3-pyridyl)-3-methylindole in 220 ml of 2N hydrochloric acid is heated under reflux for 6 hours. After cooling the solution is made basic with 3 N NaOH and extracted with ethyl acetate. The basic solution is filtered and acidified to pH 6-7 with 5 N HCl. The solid is collected, dried and recrystallized from acetone to give 1-[2-(4-carboxyphenoxy)ethyl]-2-(3-pyridyl)-3-methylindole, m.p. 190°-193°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling the solution
  4. extractionextracted with ethyl acetate
  5. filtrationThe basic solution is filtered
  6. customThe solid is collected
  7. customdried
  8. customrecrystallized from acetone

Sources & evidence

ORD record
ord-56082abe92d04ca1b721ef83bf7e9cf5
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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