Hydrochloric Acid → 9-Nitro-2,3-dihydro-4,1-benzoxazepin-5(1H)-one

HRID 1698538Notes

Reaction equation

HRID 1698538 reaction equation
OC[CH2:3][NH:4][C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8].Cl>C1COCC1.O>[N+:15]([C:14]1[C:5]2[NH:4][CH2:3][CH2:10][O:9][C:7](=[O:8])[C:6]=2[CH:11]=[CH:12][CH:13]=1)([O-:17])=[O:16]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11253443Methyl 2-[(2-hydroxyethyl)amino]-3-nitrobenzoate

Product 1

HCID 672730729-Nitro-2,3-dihydro-4,1-benzoxazepin-5(1H)-oneYield 60.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.00 g (8.32 mmol) of methyl 2-[(2-hydroxyethyl)amino]-3-nitrobenzoate in 150 mL of THF was added dropwise 6N HCl (100 mL) at 0° C. and the mixture was stirred for 30 min. The reaction mixture was refluxed for 16 h. After being cooled to room temperature, the mixture was diluted with water (150 ml), and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with aqueous sodium hydrogen sulfate and water. The organics was dried over magnesium sulfate, filtered, and concentrated in vacuo to give 1.03 g (5.00 mmol, 60%) of the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with aqueous sodium hydrogen sulfate and water
  5. dry with materialThe organics was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-248eea2a4158459ea010d7061f96103c
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

Loading…