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

HRID 2276976Notes

Reaction equation

HRID 2276976 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-57a24b39a5f74af6b2087d203ca1d10e
Source dataset
uspto-grants-2015_09
Patent number
US09133104B2

Reaction notes

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