Ethanol → HCID 21842736, compound

HRID 725965Notes

Reaction equation

HRID 725965 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH:14]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.O.[OH-].[NH4+].[CH2:28](O)[CH3:29]>>[CH2:28]([O:2][C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH:14]=1)=[O:3])[CH3:29].[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)([OH:3])=[O:2]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 190229843-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole-5-carboxylic acid

Product 1

HCID 21842736HCID 21842736, compoundYield 42%

Procedure

A solution of 0.513 gm (2 mMol) 5-carboxy-3-(1-methyl-1,2,5,6-tetrahydropyridin-4-yl)-1H-indole in 5.1 mL ethanol was cooled in an ice bath while 0.51 mL sulfuric acid was added dropwise. The resulting mixture was heated at reflux for 5 hours. The now homogeneous solution was poured into 50 mL cold water and was then made basic with saturated ammonium hydroxide. The light yellow precipitate was collected by filtration and then recrystallized from ethanol to provide 0.24 gm (42%) of the desired compound as light yellow crystals.

Workup

  1. additionwas added dropwise
  2. temperatureThe resulting mixture was heated
  3. temperatureat reflux for 5 hours
  4. filtrationThe light yellow precipitate was collected by filtration
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-9bd6ddf93a7e4ef3bf41fc0fe273f9c4
Source dataset
uspto-grants-1998_01
Patent number
US05708008

Reaction notes

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