NBD-Cl → 7-Chloro-2,1,3-benzoxadiazol-4-amine

HRID 1441805Notes

Reaction equation

HRID 1441805 reaction equation
[Cl:1][C:2]1[C:7]2=[N:8][O:9][N:10]=[C:6]2[C:5]([N+:11]([O-])=O)=[CH:4][CH:3]=1>CC(O)=O.CCOC(C)=O.O.[Fe]>[NH2:11][C:5]1[C:6]2[C:7](=[N:8][O:9][N:10]=2)[C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 1

HCID 25043NBD-Cl

Product 1

HCID 218751677-Chloro-2,1,3-benzoxadiazol-4-amineYield 94%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1.0 g (5.02 mmol) of 4-chloro-7-nitrobenzofurazan in 20 mL AcOH, 10 mL EtOAc and 2 mL H2O was heated at 50° C. and treated with iron powder (1.4 g, 251 mmol). The mixture was heated at 80° C. for 30 min and then allowed to cool to rt. The mixture was filtered through Celite eluting with EtOAc. The filtrate was washed with sat. aq. NaHCO3, dried over MgSO4, and concentrated under reduced pressure to give compound 258A (0.80 g, 94%) as a red solid.

Workup

  1. temperatureto cool to rt
  2. filtrationThe mixture was filtered through Celite
  3. washeluting with EtOAc
  4. washThe filtrate was washed with sat. aq. NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bb4ee3dd23b64e60940d8c5312313b58
Source dataset
uspto-grants-2010_02
Patent number
US07655689B2

Reaction notes

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