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

HRID 322531Notes

Reaction equation

HRID 322531 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:13]=[CH:12][C:11]2[CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[N:5]=1>FC(F)(F)C(O)=O>[N:5]1[C:6]2[NH:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=[CH:13][C:4]=1[CH:3]=[O:2]

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

14-2 (10 g, 0.048 mol) was trifluoroacetic acid (50 mL) and the resulting solution stirred under argon for 12.5 h. The TFA was removed at reduced pressure and the residue partitioned between sat. NaHCO3 and CH2Cl2. The organic layer was dried, concentrated and passed through a 3 in. pad of silica gel (10% acetone/CH2Cl2) and concentrated to afford 14-3 as a yellow crystalline solid.

Workup

  1. customThe TFA was removed at reduced pressure
  2. customthe residue partitioned between sat. NaHCO3 and CH2Cl2
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. concentrationpad of silica gel (10% acetone/CH2Cl2) and concentrated

Sources & evidence

ORD record
ord-9ca0d4a5eef84177855305c38b015e26
Source dataset
uspto-grants-2001_04
Patent number
US06211184B1

Reaction notes

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