Acetic Acid → Ethyl 5-amino-2-fluorocarbanilate

HRID 36796Notes

Reaction equation

HRID 36796 reaction equation
C(O)(=O)C.[F:5][C:6]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:7]=1[NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12]>[Fe].C(OCC)(=O)C>[NH2:18][C:15]1[CH:16]=[CH:17][C:6]([F:5])=[C:7]([CH:14]=1)[NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12]

Participants

5

Reactant 2

HCID 176Acetic Acid2×HCID 2754990Ethyl 2-fluoro-5-nitrocarbanilate

Product 1

HCID 19937926Ethyl 5-amino-2-fluorocarbanilateYield 91.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 39.4 g (706 mmol) of iron powder and 75 ml of an aqueous solution of 5% acetic acid was heated to 80° C., and a mixed solution of 16.1 g (70.6 mmol) of ethyl 2-fluoro-5-nitrocarbanilate, 72 ml of acetic acid and 72 ml of ethyl acetate was slowly added dropwise to the mixture. After the reaction was continued for 3 hours, the insolubles were filtered out and washed with ethyl acetate. Thereafter the filtrate was distilled to remove the solvent, and the resultant product was dissolved in ethyl acetate and washed with saturated sodium hydrogencarbonate, water and saturated saline solution. The solution was dried over anhydrous sodium sulfate, and the ethyl acetate was distilled off to obtain the crude product (crystals). The crude product was washed with diisopropyl ether, thereby obtaining 12.8 g of the objective product (yield: 91%) in the form of light yellow crystals.

Workup

  1. filtrationthe insolubles were filtered out
  2. washwashed with ethyl acetate
  3. distillationThereafter the filtrate was distilled
  4. customto remove the solvent
  5. dissolutionthe resultant product was dissolved in ethyl acetate
  6. washwashed with saturated sodium hydrogencarbonate, water and saturated saline solution
  7. dry with materialThe solution was dried over anhydrous sodium sulfate
  8. distillationthe ethyl acetate was distilled off
  9. customto obtain the crude product (crystals)
  10. washThe crude product was washed with diisopropyl ether

Sources & evidence

ORD record
ord-9e0ae5f97c3e4e4db558e1da3861eec0
Source dataset
uspto-grants-1995_05
Patent number
US05416236

Reaction notes

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