Sodium Hydroxide → Ethyl 2-chloro-1,8-naphthyridine-3-carboxylate

HRID 1961444Notes

Reaction equation

HRID 1961444 reaction equation
O=[C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[OH-].[Na+].O=P(Cl)(Cl)[Cl:21]>>[Cl:21][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 11564777Ethyl 2-hydroxy-1,8-naphthyridine-3-carboxylate

Product 1

HCID 15067503Ethyl 2-chloro-1,8-naphthyridine-3-carboxylateYield 55%

Procedure

Ethyl 2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate (405.0 mg, 1.86 mmol) was suspended in POCl3 (4.5 ml) under N2. The mixture was heated to reflux for 1.5 h, and then it was allowed to cool down and carefully poured over an ice-water mixture. The mixture was neutralized with solid NaOH and the product extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated. Purification was done by flash chromatography (CH2Cl2/MeOH 97:3→95:5) to give 242.6 mg (55%) of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 h
  3. temperatureto cool down
  4. extractionthe product extracted with EtOAc
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification

Sources & evidence

ORD record
ord-0d7de096a0b44f5eac238d32c9921296
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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