Methanol → HCID 20515678, compound

HRID 1902527Notes

Reaction equation

HRID 1902527 reaction equation
[C:1]([CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[C:8]1[CH:23]1[CH2:25][CH2:24]1)([O:3]C)=[O:2].[OH-].[Na+].CO>O>[C:1]([CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[C:8]1[CH:23]1[CH2:25][CH2:24]1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 20515674HCID 20515674, compound

Product 1

HCID 20515678HCID 20515678, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(2-carbomethoxyethyl)-2-cyclopropyl-3-(3-pyridylmethyl)indole (1.0 g), sodium hydroxide (0.18 g), methanol (1 ml) and water (10 ml) was heated under reflux for six hours. The resulting solution was evaporated to dryness and the residue was dissolved in a small volume of water. Acidification with acetic acid gave a solid which was filtered off, washed with water, dried and crystallised from isopropanol/petrol (b.p. 60°-80°) to give 1-(2-carboxyethyl)-2-cyclopropyl-3-(3-pyridylmethyl)indole (0.55 g), m.p. 159°-160°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for six hours
  3. customThe resulting solution was evaporated to dryness
  4. dissolutionthe residue was dissolved in a small volume of water
  5. customAcidification with acetic acid gave a solid which
  6. filtrationwas filtered off
  7. washwashed with water
  8. customdried
  9. customcrystallised from isopropanol/petrol (b.p. 60°-80°)

Sources & evidence

ORD record
ord-cf4f1065e351429088c5957cee6a601b
Source dataset
uspto-grants-1982_12
Patent number
US04363912

Reaction notes

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