Triethylamine → HCID 69217711, compound

HRID 901239Notes

Reaction equation

HRID 901239 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:26])[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:9]2[C:14]([C:15]=1O)=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])[CH3:2].C(N(CC)CC)C.O=P(Cl)(Cl)[Cl:36]>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:26])[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[C:9]2[C:14]([C:15]=1[Cl:36])=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 59699551HCID 59699551, compound

Product 1

HCID 69217711HCID 69217711, compoundYield 95%

Procedure

A solution of 4-hydroxy-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (13) (0.40 g, 1.13 mmol) and triethylamine (393 μL, 2.82 mmol) was heated in neat POCl3 at 90° C. for 3 h. The solution was cooled and the excess POCl3 was distilled under vacuum. The residue was suspended in saturated NaHCO3 solution, sonicated briefly and filtered. The solids were dissolved in dichloromethane, washed subsequently by saturated NaHCO3 solution, water and brine. The organic phase was dried over MgSO4 and evaporated to yield 400 mg (95%) of 4-chloro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (14) as white solids. 1H-NMR (DMSO-d6): δ 1.30 (t, J=7.0 Hz, 3H), 3.62 (s, 3H), 4.30 (q, J=7.0 Hz, 2H), 5.47 (s, 2H), 6.81 (d, J=7.7 Hz, 2H), 7.21 (d, J=7.6 Hz, 2H), 7.31 (d, J=7.6 Hz, 1H), 8.40 (dd, J=1.5, 7.5 Hz, 1H), 8.71 (dd, J=1.5, 7.5 Hz, 1H); EIMS: 373 (M+1).

Workup

  1. temperatureThe solution was cooled
  2. distillationthe excess POCl3 was distilled under vacuum
  3. customsonicated briefly
  4. filtrationfiltered
  5. dissolutionThe solids were dissolved in dichloromethane
  6. washwashed subsequently by saturated NaHCO3 solution, water and brine
  7. dry with materialThe organic phase was dried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-102a2722949b4c77a561e24f2d47cf33
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

Loading…