Ethyl 2-fluoro-4-nitrobenzoate → Ethyl 4-Amino-2-fluorobenzoate

HRID 369774Notes

Reaction equation

HRID 369774 reaction equation
[F:1][C:2]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]>CO>[CH2:7]([O:6][C:4](=[O:5])[C:3]1[CH:9]=[CH:10][C:11]([NH2:13])=[CH:12][C:2]=1[F:1])[CH3:8]

Participants

3

Reactant 1

HCID 10727300Ethyl 2-fluoro-4-nitrobenzoate

Product 1

HCID 10797532Ethyl 4-Amino-2-fluorobenzoateYield 93.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 250 mL round bottomed flask equipped with a magnetic stirrer were added 3.00 g of ethyl 2-fluoro-4-nitro-benzoate and 100 mL of MeOH. The solution was deoxygenated by bubbling nitrogen through for 10 min and then treated with 2.00 g of Raney nickel (Raney 3200, Davison Chemical, Chattanooga, Tenn. 37406) which had been washed with water and EtOH. The solution was subjected to hydrogenation at 1 atm with stirring for 40 min. The flask was purged with nitrogen and the catalyst was removed by filtration. The filtrate was concentrated in vacuo to afford 2.40 g (93%) of ethyl-4-amino-2-fluorobenzoate as a tan crystalline solid, m.p. 110-112° C.

Workup

  1. customTo a 250 mL round bottomed flask equipped with a magnetic stirrer
  2. customThe solution was deoxygenated
  3. customby bubbling nitrogen through for 10 min
  4. additiontreated with 2.00 g of Raney nickel (Raney 3200, Davison Chemical, Chattanooga, Tenn. 37406) which
  5. washhad been washed with water and EtOH
  6. customThe flask was purged with nitrogen
  7. customthe catalyst was removed by filtration
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ae628b44c7e148cab5da7c8a5739309c
Source dataset
uspto-grants-2000_10
Patent number
US06140100

Reaction notes

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