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

HRID 379229Notes

Reaction equation

HRID 379229 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-81333ece685042648560ab860a57270d
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Reaction notes

Loading…