7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine → 5,6,7,8-Tetrahydro-1,8-naphthyridine-2-carbaldehyde
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]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
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
- customThe mixture was quenched with saturated sodium bicarbonate
- extractionextracted with methylene chloride
- dry with materialdried over sodium sulfate
- filtrationfiltered, in vacuo
- 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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