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

HRID 1004249Notes

Reaction equation

HRID 1004249 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

8-2 (10 g, 0.048 mol) was treated with 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 8-3 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-9c80565faa13457dbc8884faab12ec2e
Source dataset
uspto-grants-2000_04
Patent number
US06048861

Reaction notes

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