Formaldehyde → 1,8-Dimethyl-1,2,3,4-tetrahydroquinoline-5-carboxylic acid

HRID 1017131Notes

Reaction equation

HRID 1017131 reaction equation
[C:1]([BH3-])#N.[Na+].[CH3:5][C:6]1[C:15]2[NH:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:9]([C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1.C=O.[OH-].[Na+]>C(O)(=O)C>[CH3:1][N:14]1[C:15]2[C:6]([CH3:5])=[CH:7][CH:8]=[C:9]([C:16]([OH:18])=[O:17])[C:10]=2[CH2:11][CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 139517338-Methyl-1,2,3,4-tetrahydroquinoline-5-carboxylic acid

Product 1

HCID 184030301,8-Dimethyl-1,2,3,4-tetrahydroquinoline-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

24 mmol of sodium cyanoborohydride w&e added to 5 mmol of 8-methyl-1,2,3,4-tetrahydroquinoline-5-carboxylic acid and 50 mmol of paraformaldehyde in 30 ml of glacial acetic acid, the temperature of the reaction mixture being kept below 30° C. using an ice bath. The reaction mixture was stirred at room temperature for 15 hours, poured onto ice and adjusted to pH 4 with aqueous sodium hydroxide solution. The mixture was then extracted with ethyl acetate and the organic phase was washed with water, dried over sodium sulfate and concentrated.

Workup

  1. custombeing kept below 30° C.
  2. additionpoured onto ice
  3. extractionThe mixture was then extracted with ethyl acetate
  4. washthe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f6b6add095d84efa84927ae81a3836e8
Source dataset
uspto-grants-2002_11
Patent number
US06479436B1

Reaction notes

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