Sodium Bicarbonate → 3-Amino-2,4-dichloro-5-fluorobenzamide

HRID 450330Notes

Reaction equation

HRID 450330 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-])=O)=[C:9]([Cl:14])[C:8]([F:15])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C([O-])(O)=O.[Na+]>CCOC(C)=O>[Cl:1][C:2]1[C:10]([NH2:11])=[C:9]([Cl:14])[C:8]([F:15])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 866744942,4-Dichloro-5-fluoro-3-nitrobenzamide

Product 1

HCID 866744963-Amino-2,4-dichloro-5-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,4-dichloro-5-fluoro-3 nitro-benzamide (7.00 g, 27.7 mmol), Sn(II)Cl2×2H2O (28 g, 124 mmol) and EtOAc (250 mL) is stirred for 3 h at reflux and then carefully added to a sat. aq. NaHCO3-solution (250 mL). The resulting mixture is filtered through a pad of celite, the organic phase is separated and washed with brine, dried with MgSO4 and concentrated.

Workup

  1. temperatureat reflux
  2. filtrationThe resulting mixture is filtered through a pad of celite
  3. customthe organic phase is separated
  4. washwashed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9d41a2f0a67b44858ebfc8622a5ce4e3
Source dataset
uspto-grants-2013_07
Patent number
US08486968B2

Reaction notes

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