Sodium Hydroxide → HCID 66633913, compound

HRID 1961464Notes

Reaction equation

HRID 1961464 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10](=O)[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:7]=[CH:6][N:5]=2.[OH-].[Na+].O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:10]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([CH3:1])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 11085642HCID 11085642, compound

Product 1

HCID 66633913HCID 66633913, compoundYield 95%

Conditions

Temperature
100 °C

Procedure

Ethyl 2-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (5.18 mg, 2.23 mmol) was dissolved in POCl3. The mixture was heated to 100° C. for 1.0 h. The mixture was allowed to cool and then it was carefully poured into ice-water (250 ml). The mixture was neutralized with solid NaOH. The product was extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated. Purification was done by flash chromatography (CH2Cl2/MeOH 97:3→96:4) giving 531 mg (95%) of the title compound.

Workup

  1. temperatureto cool
  2. extractionThe product was extracted with EtOAc
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-44f2770df1e24de0a080e4ce4de6f923
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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