2-(Methylamino)ethanol → HCID 14983970, compound

HRID 864402Notes

Reaction equation

HRID 864402 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]1[C:22]([OH:24])=O.[CH3:25][NH:26][CH2:27][CH2:28][OH:29]>O1CCCC1>[CH3:25][N:26]([CH2:27][CH2:28][OH:29])[C:22]([C:14]1[NH:13][C:21]2[C:16]([CH:15]=1)=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:24]

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 682631,1'-CarbonyldiimidazoleHCID 72899Indole-2-carboxylic acid

Product 1

HCID 14983970HCID 14983970, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1'-carbonyldiimidazole (1.11 g) is added to a solution of indole-2-carboxylic acid (1.0 g) in tetrahydrofuran (15 ml). The mixture is stirred 1 hour at 20°-25° and 2-(methylamino)ethanol (5.0 ml) is added. The mixture is stirred 21 hours at 20°-25° and 24 hours at reflux. The mixture is concentrated under reduced pressure, diluted with methylene chloride and extracted with water and saturated sodium bicarbonate. The phases are separated and the organic phase is dried with saline and sodium sulfate and concentrated to give the crude product. Chromatography on silica gel with a methanol/chloroform gradient followed by recrystallization from chloroform/ether to give the title compound, mp 141°-142.5°.

Workup

  1. stirringThe mixture is stirred 21 hours at 20°-25° and 24 hours
  2. temperatureat reflux
  3. concentrationThe mixture is concentrated under reduced pressure
  4. additiondiluted with methylene chloride
  5. extractionextracted with water and saturated sodium bicarbonate
  6. customThe phases are separated
  7. dry with materialthe organic phase is dried with saline and sodium sulfate
  8. concentrationconcentrated
  9. customto give the crude product
  10. customChromatography on silica gel with a methanol/chloroform gradient followed by recrystallization from chloroform/ether

Sources & evidence

ORD record
ord-c6492ddcf2684b59b2949d8fe501bee2
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

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