Hydrochloric Acid → 2,3,4,9-Tetrahydro-1H-pyrido(3,4-b)indole-1-carboxylic acid

HRID 2360631Notes

Reaction equation

HRID 2360631 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=O.[NH2:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1.Cl.[OH-].[K+]>O>[CH:3]1([C:2]([OH:6])=[O:5])[C:11]2[NH:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]=2[CH2:9][CH2:8][NH:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1150TryptamineHCID 14797Potassium HydroxideHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 1458792,3,4,9-Tetrahydro-1H-pyrido(3,4-b)indole-1-carboxylic acidYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A solution of glyoxylic acid monohydrate (1.51 g, 16.4 mmol) in water (10 ml) was added dropwise to a stirred solution of tryptamine.HCl (3.0 g, 15.3 mmol) in water (200 ml). KOH (0.827 g, 14.7 mmol) in water (10 ml) was added. The reaction mixture was stirred at room temperature for 1 h after which time precipitation occurred. Following filtration under reduced pressure the white precipitate was collected and washed with water to furnish 2,3,4,9-tetrahydro-1H-beta-carboline-1-carboxylic acid Yield 1.9 g (58%); m/z 217 [M++H]+.

Workup

  1. customafter which time precipitation
  2. filtrationfiltration under reduced pressure the white precipitate
  3. customwas collected
  4. washwashed with water

Sources & evidence

ORD record
ord-2a5386a025d64d72b414d1ccd0d7b4d1
Source dataset
uspto-grants-2014_04
Patent number
US08686032B2

Reaction notes

Loading…