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Butanal → 1-propyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid

HRID 1619471
Notes
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Reaction equation

HRID 1619471 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.O.OS(O)(=O)=O.[CH:22](=O)[CH2:23][CH2:24][CH3:25]>C(O)C>[CH2:23]([CH:22]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)[CH2:24][CH3:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 261ButanalHCID 962WaterHCID 1118Sulfuric AcidHCID 6305L-Tryptophan

Product 1

HCID 31618321-propyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acidYield 58%

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

Procedure

L-tryptophan (5.10 g, 25 mmol), water (300 ml), H2SO4 (0.5M, 50 ml), n-butyraldehyde (10 ml) and ethanol (100 ml) were added in a 250 ml round-bottom flask, and then stirred and reacted at room temperature for 24 h. After filtration, wash with water and drying, white solids (3.75 g, 58%) were obtained.

Workup

  1. customreacted at room temperature for 24 h
  2. filtrationAfter filtration
  3. washwash with water
  4. customdrying

Sources & evidence

ORD record
ord-412de87610234ca8bc04e06223598e84
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772311B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes