Acetaldehyde → 1-Methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

HRID 1619469Notes

Reaction equation

HRID 1619469 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.[CH:16](=O)[CH3:17]>OS(O)(=O)=O>[CH3:16][CH:17]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

Participants

4

Reactant 2

HCID 177AcetaldehydeHCID 6305L-Tryptophan

Product 1

HCID 735301-Methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acidYield 69%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

L-tryptophan (5.10 g, 25 mmol), H2SO4 (0.01 M, 30 ml) and 40% acetaldehyde (9 ml) were added in a 250 ml round-bottom flask, and then stirred and reacted at room temperature for 8 h. After filtration, wash with water and drying, white solids (4.0 g, 69%) were obtained.

Workup

  1. customreacted at room temperature for 8 h
  2. filtrationAfter filtration
  3. washwash with water
  4. customdrying

Sources & evidence

ORD record
ord-60e9dfb5241d42b3a6bfe60e4c0a460c
Source dataset
uspto-grants-2014_07
Patent number
US08772311B2

Reaction notes

Loading…