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

HRID 1385045Notes

Reaction equation

HRID 1385045 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 were 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 being kept below 30° C. using an ice bath. The mixture was stirred at room temperature for 15 hours and then poured onto ice and adjusted to pH 4 using 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-8e5e53f6f5214121a8652b65a04e62a1
Source dataset
uspto-grants-2001_07
Patent number
US06262074B1

Reaction notes

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