4,6-Dichloro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl Ester → 4,6-Dichloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl Ester

HRID 901258Notes

Reaction equation

HRID 901258 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:27])[N:8](CC2C=CC(OC)=CC=2)[C:9]2[C:14]([C:15]=1[Cl:16])=[CH:13][C:12]([Cl:17])=[CH:11][N:10]=2)=[O:5])[CH3:2]>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:27])[NH:8][C:9]2[C:14]([C:15]=1[Cl:16])=[CH:13][C:12]([Cl:17])=[CH:11][N:10]=2)=[O:5])[CH3:2]

Participants

3

Reactant 1

HCID 692156984,6-Dichloro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl Ester

Product 1

HCID 692172654,6-Dichloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic Acid Ethyl EsterYield 99.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4,6-dichloro-1-(4-methoxy-benzyl)-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (77) (6.0 g, 14.73 mmol) in neat TFA was refluxed for 3 h. The solution was cooled and the excess TFA was distilled under vacuum. The residue was suspended in saturated NaHCO3 solution, sonicated briefly and filtered. The solids were washed by water, and dried at room temperature to yield 4.2 g (99%) of 4,6-dichloro-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (79) as white solids. MP: 228° C.; 1H-NM (DMSO-d6): δ 1.29 (t, J=7.2 Hz, 3H), 4.37 (q, J=7.2 Hz, 2H), 8.38 (d, J=2.4 Hz, 1H), 8.75 (d, J=2.4 Hz, 1H), 13.10 (s, 1H); EIMS: 287 (M).

Workup

  1. temperatureThe solution was cooled
  2. distillationthe excess TFA was distilled under vacuum
  3. customsonicated briefly
  4. filtrationfiltered
  5. washThe solids were washed by water
  6. customdried at room temperature

Sources & evidence

ORD record
ord-01087b1a715846d4928c103158c993db
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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