Sodium ethoxide → 6-methyl-7-(propan-2-yloxy)-3,4-dihydropyrido[4,3-f][1,4]oxazepin-5(2H)-one

HRID 577586Notes

Reaction equation

HRID 577586 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[C:6]([C:16]([O:18]C)=O)=[C:7]([CH3:15])[C:8]([O:11][CH:12]([CH3:14])[CH3:13])=[N:9][CH:10]=1.CC[O-].[Na+]>CCO>[CH3:15][C:7]1[C:6]2[C:16](=[O:18])[NH:1][CH2:2][CH2:3][O:4][C:5]=2[CH:10]=[N:9][C:8]=1[O:11][CH:12]([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 86723813Methyl 5-(2-aminoethoxy)-3-methyl-2-(propan-2-yloxy)pyridine-4-carboxylate

Product 1

HCID 867238126-methyl-7-(propan-2-yloxy)-3,4-dihydropyrido[4,3-f][1,4]oxazepin-5(2H)-oneYield 65.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 5-(2-aminoethoxy)-3-methyl-2-(propan-2-yloxy)pyridine-4-carboxylate (131e, 1.2 g, 2.2 mmol) and NaOEt (3.0 g, 45 mmol) in dry EtOH (60 mL) was refluxed for 14 hours. The reaction mixture was concentrated under vacuum. The residue was dissolved in H2O (30 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4, and concentrated under vacuum to give 6-methyl-7-(propan-2-yloxy)-3,4-dihydropyrido[4,3-f][1,4]oxazepin-5(2H)-one (131f, 0.34 g) as a brown solid.

Workup

  1. temperaturewas refluxed for 14 hours
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. dissolutionThe residue was dissolved in H2O (30 mL)
  4. extractionextracted with EtOAc (2×20 mL)
  5. washThe combined organic layers were washed with brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-018b26233821484c94848e07380e7e7d
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

Loading…