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

HRID 548234Notes

Reaction equation

HRID 548234 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-5b2e865880cf4efda599ff848e917205
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

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