Hydrogen Bromide → HCID 178448441, compound

HRID 1441495Notes

Reaction equation

HRID 1441495 reaction equation
[C:1]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][N:9]=[C:10]([O:15]C)[CH:11]=2)[CH2:6]1)([CH3:4])([CH3:3])[CH3:2].Br>C(O)(=O)C>[C:1]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][N:9]=[C:10]([OH:15])[CH:11]=2)[CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 442276722-(1,1-Dimethylethyl)-1,2,3,4-tetrahydro-6-methoxy-2,7-naphthyridine

Product 1

HCID 178448441HCID 178448441, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-tert-butyl-6-methoxy-1,2,3,4-tetrahydro-2,7-naphthyridine (5.1 g, 23 mmol) and 45% hydrobromic acid in acetic acid (70 mL) was heated in a sealed tube at 100° C. for 1 h, cooled to RT and concentrated. The residue was dissolved carefully in 20% potassium carbonate solution (100 mL) and extracted four times with EtOAc. The combined organic phases were dried, filtered and concentrated. Recrystallisation from TBME-hexanes gave 3.7 g (77%) of the title compound as a white solid.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved carefully in 20% potassium carbonate solution (100 mL)
  3. extractionextracted four times with EtOAc
  4. customThe combined organic phases were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customRecrystallisation from TBME-hexanes

Sources & evidence

ORD record
ord-9e10929e2730498c820abf8dc3040884
Source dataset
uspto-grants-2010_02
Patent number
US07655664B2

Reaction notes

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