Ethanol → 4-oxo-3-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde

HRID 1811244Notes

Reaction equation

HRID 1811244 reaction equation
C(O[C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][NH:8][C:7]=1[CH2:17][CH2:18][NH2:19])=[O:5])C.O.[OH-].[Li+].O.[CH2:24]([OH:26])C>>[O:5]=[C:4]1[C:6]2[C:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[C:9]([CH:24]=[O:26])[NH:8][C:7]=2[CH2:17][CH2:18][NH:19]1

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 666081252-(2-amino-ethyl)-4-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 866376804-oxo-3-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehydeYield 38.9%

Procedure

A stirred solution of 2-(2-amino-ethyl)-4-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester, lithium hydroxide monohydrate (840 mg, 20 mmol) in ethanol (20 ml) was heated to reflux under an argon atmosphere for 3 hours. The mixture was added with cold water (150 ml), stirred for 10 minutes, extracted with dichloromethane:methanol=5:1 (50 ml×7), washed with brine, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was recrystallized from dichloromethane and methanol to give 4-oxo-3-phenyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carbaldehyde (280 mg, 38.9%) as a red solid.

Workup

  1. temperatureto reflux under an argon atmosphere for 3 hours
  2. extractionextracted with dichloromethane
  3. washmethanol=5:1 (50 ml×7), washed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was recrystallized from dichloromethane and methanol

Sources & evidence

ORD record
ord-7e80d8e3267e4838ada6b9cdce0d8e02
Source dataset
uspto-grants-2013_01
Patent number
US08362251B2

Reaction notes

Loading…