Formaldehyde → 1-Methyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

HRID 2356760Notes

Reaction equation

HRID 2356760 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:14]=O>CN(C)C=O.[C].[Pd]>[CH3:14][N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 27796411,2,3,4-Tetrahydroquinoline-6-carboxylic acid

Product 1

HCID 33757681-Methyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,2,3,4-tetrahydroquinolin-6-carboxylic acid (2 g), 32% aqueous formalin solution (2 ml) and 10% palladium-carbon (400 mg) in N,N-dimethylformamide (10 ml) was stirred under hydrogen atmosphere at room temperature for one hour. After removing the palladium-carbon by filtration, the solvent was removed under reduced pressure and the resulting residue was triturated with diethyl ether to obtain 1-methyl-1,2,3,4-tetrahydroquinolin-6-carboxylic acid (1.98 g) as yellowish powder.

Workup

  1. customAfter removing the palladium-carbon
  2. filtrationby filtration
  3. customthe solvent was removed under reduced pressure
  4. customthe resulting residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-16340a8efd4c4fda9cc4fffb735c54ea
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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