Ammonium Chloride → HCID 66617763, compound

HRID 2263521Notes

Reaction equation

HRID 2263521 reaction equation
[CH2:1]1[CH2:3][CH:2]1[CH:4]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[C:12]([N+:15]([O-])=O)[CH:13]=[CH:14][C:6]=2[O:5]1.[Cl-].[NH4+]>CCO.O.ClCCl.[Fe]>[NH2:15][C:12]1[CH:13]=[CH:14][C:6]2[O:5][CH:4]([CH:2]3[CH2:3][CH2:1]3)[C:9](=[O:10])[NH:8][C:7]=2[CH:11]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 66617677HCID 66617677, compound

Product 1

HCID 66617763HCID 66617763, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 6344DichloromethaneSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 200 mg of 2-(2-cyclopropyl)-6-nitro-3-oxo-4H-benz[1,4]oxazine (1 g) in EtOH/water (20 mL; 2:1 v/v) was added 5 eq of iron and 5 eq of ammonium chloride and the reaction was heated at 90° C. for 4 h. The reaction mixture was cooled to room temperature, diluted with dichloromethane and filtered. The layers were separated, the aqueous was extracted once with dichloromethane, the combined organics layers were dried over magnesium sulfate, the solution filtered and the filtrate evaporated in vacuo to give the desired product 6-amino-2-(2-cyclopropyl)-3-oxo-4H-benz[1,4]. MS (m/e): 191 (MH+).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customThe layers were separated
  4. extractionthe aqueous was extracted once with dichloromethane
  5. dry with materialthe combined organics layers were dried over magnesium sulfate
  6. filtrationthe solution filtered
  7. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-4b1eee1b1c0d4d96848efddd60e72303
Source dataset
uspto-grants-2010_12
Patent number
US07851480B2

Reaction notes

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