Ammonium Chloride → 6-amino-4-fluoro-3-methyl-1,3-benzoxazol-2(3H)-one

HRID 896201Notes

Reaction equation

HRID 896201 reaction equation
[F:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[O:10][C:6]=2[CH:5]=[C:4]([N+:13]([O-])=O)[CH:3]=1.[Cl-].[NH4+]>C(O)C.O.ClCCl.[Fe]>[NH2:13][C:4]1[CH:3]=[C:2]([F:1])[C:7]2[N:8]([CH3:12])[C:9](=[O:11])[O:10][C:6]=2[CH:5]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 684871524-fluoro-3-methyl-6-nitro-1,3-benzoxazol-2(3H)-one

Product 1

HCID 684860356-amino-4-fluoro-3-methyl-1,3-benzoxazol-2(3H)-one

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Iron powder (0.77 g, 0.0138 mol) is added in small portions to a mixture of 4-fluoro-3-methyl-6-nitro-1,3-benzoxazol-2(3H)-one (Step 6, 0.73 g, 3.44 mmol) and ammonium chloride (1.84 g, 3.44 mmol) in ethanol (30 ml) and water (15 ml) at 95° C. The reaction mixture is stirred vigorously and heated for 1 h, cooled to room temperature, and diluted with dichloromethane (150 ml). The mixture is filtered, washed with water and saline, dried (MgSO4) and evaporated to give product as a tan solid suitable for use in the next step (0.64 g, 99%).

Workup

  1. temperatureheated for 1 h
  2. filtrationThe mixture is filtered
  3. washwashed with water and saline
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give product as a tan solid suitable for use in the next step (0.64 g, 99%)

Sources & evidence

ORD record
ord-d7c16bef64d04a6ca956fc23935320bb
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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