Methanol → 7-amino-6-chloro-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 970654Notes

Reaction equation

HRID 970654 reaction equation
[Cl:1][C:2]1[C:12]([N+:13]([O-])=O)=[CH:11][C:5]2[O:6][CH2:7][C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.CCOC(C)=O.CO.CCN(CC)CC>CN(C=O)C>[NH2:13][C:12]1[C:2]([Cl:1])=[CH:3][C:4]2[NH:9][C:8](=[O:10])[CH2:7][O:6][C:5]=2[CH:11]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 33056966-Chloro-7-nitro-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 141762577-amino-6-chloro-3,4-dihydro-2H-1,4-benzoxazin-3-oneYield 48.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stannous chloride dihydrate (30 g, 0.13 mol) was added in portion to a solution of 6-chloro-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one (6.7 g, 0.026 mol) in DMF (100 mL) with ice bath cooling. The mixture was allowed to warm to room temperature and was then stirred overnight. EtOAc (300 mL) and MeOH (300 mL) were added to the reaction mixture, Et3N was added until pH>8 and the resulting suspension was filtered through celite. The solvent was removed under vacuum and the residue was suspended in water, extracted with EtOAc, dried (Na2SO4), filtered and concentrated under vacuum. The residue was triturated with ether to give the product (2.5 g, 45%) as a yellow solid.

Workup

  1. temperaturecooling
  2. additionwas added until pH>8
  3. filtrationthe resulting suspension was filtered through celite
  4. customThe solvent was removed under vacuum
  5. extractionextracted with EtOAc
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-a076a97625754a5cb62a813dd26ddbfe
Source dataset
uspto-grants-2007_12
Patent number
US07312233B2

Reaction notes

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