Propanal → 1-Ethyl-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acid

HRID 1619470Notes

Reaction equation

HRID 1619470 reaction equation
[NH2:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.OS(O)(=O)=O.[CH:21](=O)[CH2:22][CH3:23]>O>[CH2:22]([CH:23]1[C:5]2[NH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]=2[CH2:3][CH:2]([C:13]([OH:15])=[O:14])[NH:1]1)[CH3:21]

Participants

5

Reactant 3

HCID 527PropanalHCID 1118Sulfuric AcidHCID 6305L-Tryptophan

Product 1

HCID 31432881-Ethyl-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylic acidYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

L-tryptophan (5.10 g, 25 mmol), water (300 ml), H2SO4 (0.05M, 30 ml) and propionaldehyde (8 ml) were added in a 250 ml round-bottom flask, and then stirred and reacted at room temperature for 24 h. After filtration, wash with water and drying, white solids (4.5 g, 74%) were obtained.

Workup

  1. customreacted at room temperature for 24 h
  2. filtrationAfter filtration
  3. washwash with water
  4. customdrying

Sources & evidence

ORD record
ord-ca996683194049e99c65f90b7ad4bcc7
Source dataset
uspto-grants-2014_07
Patent number
US08772311B2

Reaction notes

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