Sodium ethoxide → Ethyl 1-(benzyloxy)-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

HRID 601159Notes

Reaction equation

HRID 601159 reaction equation
[CH2:1]([O:8][N:9]([C:21](=[O:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:10]1[N:20]=[CH:19][CH:18]=[CH:17][C:11]=1[C:12]([O:14]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]CC.[Na+]>C(O)C>[CH2:1]([O:8][N:9]1[C:10]2[C:11](=[CH:17][CH:18]=[CH:19][N:20]=2)[C:12]([OH:14])=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:21]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 86592121Ethyl 2-[(benzyloxy)(3-ethoxy-3-oxopropanoyl)amino]nicotinate

Product 1

HCID 59224799Ethyl 1-(benzyloxy)-4-hydroxy-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylateYield 82.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of the product of Example 157B (0.386 g, 1.0 mmol) in ethanol (5 mL) was treated with 21% sodium ethoxide in ethanol (0.324 g, 1.0 mmol), stirred for 30 minutes and partitioned between ethyl acetate and 5% aqueous HCl and the layers were separated. The ethyl acetate layer was washed with brine, dried (Na2SO4), and concentrated to provide the title compound (0.28 g, 82%). MS (DCI) m/z 341(M+H)+.

Workup

  1. custompartitioned between ethyl acetate and 5% aqueous HCl
  2. customthe layers were separated
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7990118a0388443e914fec2d235c1216
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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