7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine → 5,6,7,8-Tetrahydro-1,8-naphthyridine-2-carbaldehyde

HRID 1057502Notes

Reaction equation

HRID 1057502 reaction equation
C[O:2][CH:3](OC)[C:4]1[N:9]=[C:8]2[NH:10][CH2:11][CH2:12][CH2:13][C:7]2=[CH:6][CH:5]=1>FC(F)(F)C(O)=O>[NH:10]1[C:8]2=[N:9][C:4]([CH:3]=[O:2])=[CH:5][CH:6]=[C:7]2[CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 1

HCID 177501767-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine

Product 1

HCID 218737255,6,7,8-Tetrahydro-1,8-naphthyridine-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Dimethoxy-1,2,3,4-tetrahydropyridino[2,3-b]pyridin-7-ylmethane was dissolved in trifluoroacetic acid (14 mL) and stirred under nitrogen for 16 hrs. The mixture was quenched with saturated sodium bicarbonate, extracted with methylene chloride, dried over sodium sulfate, filtered, in vacuo and purified by flash chromatography (5% MeOH/CH2Cl2 ). EI-MS m/z 163 (M+H)+.

Workup

  1. customThe mixture was quenched with saturated sodium bicarbonate
  2. extractionextracted with methylene chloride
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered, in vacuo
  5. custompurified by flash chromatography (5% MeOH/CH2Cl2 )

Sources & evidence

ORD record
ord-8f6e0f92abb04482939c2ad86e76e799
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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