1,4-Dioxane → Ethyl (7-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-yl)acetate

HRID 1054175Notes

Reaction equation

HRID 1054175 reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[N:6](C(OC(C)(C)C)=O)[CH:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:8][O:9][C:4]=2[CH:3]=1.O1CCOCC1>Cl>[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[NH:6][CH:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 131736332tert-Butyl 7-bromo-3-(2-ethoxy-2-oxoethyl)-2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate2×

Product 1

HCID 118599776Ethyl (7-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-yl)acetateYield 96%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

tert-Butyl 7-bromo-3-(2-ethoxy-2-oxoethyl)-2,3-dihydro-4H-1,4-benzoxazine-4-carboxylate (Intermediate 24, 556 mg, 1.39 mmol) was dissolved in hydrogen chloride in dioxane (5.0 mL, 162.8 mmol) and the mixture stirred for 2 h at rt. The solvent was evaporated and the residue dissolved in EtOAc (50 mL), washed with sat. aq. Na2CO3 (30 mL) and brine (20 mL), dried over Na2SO4 and evaporated after filtration to give the title compound (399 mg, 96%) as an oil.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in EtOAc (50 mL)
  3. washwashed with sat. aq. Na2CO3 (30 mL) and brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. filtrationafter filtration

Sources & evidence

ORD record
ord-a32f42099c594256b5d772651932e7a7
Source dataset
uspto-grants-2016_07
Patent number
US09394291B2

Reaction notes

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