Hydrochloric Acid → 1,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic Acid

HRID 1619468Notes

Reaction equation

HRID 1619468 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.[OH-].[Na+].[CH2:18]=O.Cl>O>[CH2:18]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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 6305L-TryptophanHCID 14798Sodium Hydroxide

Product 1

HCID 982851,2,3,4-Tetrahydro-Beta-Carboline-3-Carboxylic AcidYield 85.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

L-tryptophan (10.2 g, 50 mmol), NaOH (2.0 g, 50 mmol) and H2O (20 ml) were added in a 250 ml round-bottom flask, and were stirred until the mixture became clear followed by the addition of formaldehyde (37%, 50 mmol). The mixture was stirred and reacted at room temperature for 3 h. After being refluxed for another 3 h, the mixture was poured into 200 ml cold water. While being stirred, the mixture was adjusted to pH 6 with 5N HCl. White solids were precipitated and then stored at 4° C. overnight. The white solids were filtered, washed well with water and a small amount of methanol, dried, and recrystallized with methanol to obtain white solids (9.2 g, 85%), mp 308-309° C. (reference: 309-310° C.).

Workup

  1. stirringThe mixture was stirred
  2. customreacted at room temperature for 3 h
  3. temperatureAfter being refluxed for another 3 h
  4. stirringWhile being stirred
  5. customWhite solids were precipitated
  6. filtrationThe white solids were filtered
  7. washwashed well with water
  8. dry with materiala small amount of methanol, dried
  9. customrecrystallized with methanol

Sources & evidence

ORD record
ord-99946076914e4fdd8306ee7b778749bd
Source dataset
uspto-grants-2014_07
Patent number
US08772311B2

Reaction notes

Loading…