Ethanol → HCID 46914009, compound

HRID 597845Notes

Reaction equation

HRID 597845 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[C:14]2[C:13](=[O:15])[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][CH:7]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.[CH2:21](O)[CH3:22]>>[CH2:21]([O:2][C:1](=[O:3])[CH2:4][CH2:5][C:6]1[C:14]2[C:13](=[O:15])[CH2:12][CH2:11][CH2:10][C:9]=2[NH:8][CH:7]=1)[CH3:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 158327213-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoic acid

Product 1

HCID 46914009HCID 46914009, compoundYield 99%

Procedure

3-Carboxyethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole (3, 52.0 g, 0.251 mol) in ethanol (100 mL) was added with sulfuric acid (1.0 mL). The reaction mixture was heated at reflux for 12 h. The solution was concentrated under reduced pressure and the resultant solids were washed with water (200 mL×2). The solids were air-dried to give 3-(3-ethoxy-3-oxopropyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole (4, 59.0 g, 0.251 mol) as yellow solids in >99% yield.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 12 h
  3. concentrationThe solution was concentrated under reduced pressure
  4. washthe resultant solids were washed with water (200 mL×2)
  5. customThe solids were air-dried

Sources & evidence

ORD record
ord-c2e866c8818e4e0d91f3499cf7eebf1d
Source dataset
uspto-grants-2011_03
Patent number
US07897602B2

Reaction notes

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