Water → 3-(2-Aminobenzyl)-6-phenyl-[1,3]-oxazinan-2-one

HRID 553393Notes

Reaction equation

HRID 553393 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:9][C:8]1=[O:19])([O-])=O.[Cl-].[NH4+].O>C(O)C.[Fe]>[NH2:1][C:4]1[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=1[CH2:6][N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:9][C:8]1=[O:19]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 674595203-(2-Nitrobenzyl)-6-phenyl-[1,3]-oxazinan-2-one

Product 1

HCID 674620163-(2-Aminobenzyl)-6-phenyl-[1,3]-oxazinan-2-oneYield 99.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

3-(2-Nitrobenzyl)-6-phenyl-[1,3]-oxazinan-2-one (1.59 g, 5.10 mmol), iron powder (1.42 g, 25.4 mmol), ammonium chloride (0.14 g, 2.62 mmol) were suspended in ethanol (30 ml) and water (15 ml) and heated to reflux for 1.5 hours. After cooling to room temperature, the reaction mixture was filtered with suction and extracted with ethyl acetate. The organic layer was washed with a saturated brine and then dried over anhydrous sodium sulfate, and 3-(2-aminobenzyl)-6-phenyl-[1,3]-oxazinan-2-one (1.43 g) was obtained by evaporating the solvent under reduced pressure.

Workup

  1. temperatureto reflux for 1.5 hours
  2. filtrationthe reaction mixture was filtered with suction
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated brine
  5. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-279427bedc5d4d239b00cc6dfc2c8131
Source dataset
uspto-grants-2011_11
Patent number
US08048825B2

Reaction notes

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