Sulfuric Acid → Beta-Carboline

HRID 499255Notes

Reaction equation

HRID 499255 reaction equation
[NH2:1][C@H:2](C(O)=O)[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[CH3:16]OC1C=C(C=CC=1)C=O.S(=O)(=O)(O)O>C(#N)C>[CH:16]1[C:5]2[NH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]=2[CH:3]=[CH:2][N:1]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6305L-TryptophanHCID 115693-Methoxybenzaldehyde

Product 1

HCID 64961Beta-Carboline

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tryptophan A (1.0 g, 5.0 mmol) and 3-methoxybenzaldehyde (670 μL, 5.5 mmol) are suspended/dissolved in acetonitrile (100 mL) and concentrated sulfuric acid (100 μL) is added. The reaction is heated to reflux until all the aldehyde was consumed (overnight). The solvent was removed in vacuo and the residue was dissolved in 5 mL of ethanol. The product was precipitated out with ether, filtered, and washed with 10 mL of ether. The desired β-carboline product/intermediate B (1-(3-Methoxy-phenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid) is isolated as a beige solid (1.2 g, 76%). LC/MS RT=2.33 min. M/Z+323, 100%.

Workup

  1. temperatureThe reaction is heated
  2. customwas consumed (overnight)
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in 5 mL of ethanol
  5. customThe product was precipitated out with ether
  6. filtrationfiltered
  7. washwashed with 10 mL of ether

Sources & evidence

ORD record
ord-ede9940a2091461485202d8c6ccf1568
Source dataset
uspto-grants-2010_08
Patent number
US07767689B2

Reaction notes

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