5-Fluoro-2-nitrobenzamide → 2-Amino-5-fluorobenzamide

HRID 717356Notes

Reaction equation

HRID 717356 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-])=O)=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8]>CO.[C].[Pd]>[NH2:11][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:10][C:6]=1[C:7]([NH2:9])=[O:8]

Participants

4

Reactant 1

HCID 186681655-Fluoro-2-nitrobenzamide

Product 1

HCID 102410032-Amino-5-fluorobenzamide

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Into a 500-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a mixture of 5-fluoro-2-nitrobenzamide (17.5 g, 95.04 mmol, 1.00 equiv) and palladium carbon (10%) (1.75 g, 0.10 equiv) in methanol (150 mL). To the above H2 (enough) was introduced. The resulting solution was stirred for 2 h at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 12.0 g (82%) of 2-amino-5-fluorobenzamide as a white solid. MS (ESI) m/z 155 ([M+H]+).

Workup

  1. customInto a 500-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. additionTo the above H2 (enough) was introduced
  4. filtrationThe solids were filtered out
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. customThis resulted in 12.0 g (82%) of 2-amino-5-fluorobenzamide as a white solid

Sources & evidence

ORD record
ord-5f6f48a50d274c01bfc8971746968c2d
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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