Acetic Acid → 2-(2-Methylpropylamino)-4-ethoxycarbonylamino-5-fluoroaniline

HRID 2258620Notes

Reaction equation

HRID 2258620 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][NH:4][C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][C:8]([F:14])=[C:7]([NH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:6]=1.C(O)(=O)C.Cl>C(O)C.[Fe]>[CH3:21][CH:2]([CH3:1])[CH2:3][NH:4][C:5]1[CH:6]=[C:7]([NH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]([F:14])=[CH:9][C:10]=1[NH2:11]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 22921553N-(2-methylpropyl)-3-ethoxycarbonylamino-4-fluoro-6-nitroaniline

Product 1

HCID 229215322-(2-Methylpropylamino)-4-ethoxycarbonylamino-5-fluoroanilineYield 82.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A stirred mixture of 2.7 grams (0.009 mole) of N-(2-methylpropyl)-3-ethoxycarbonylamino-4-fluoro-6-nitroaniline, 2.0 grams (0.036 mole) of iron powder, 15 mL of acetic acid, and 0.5 mL (0.009 mole) of concentrated hydrochloric acid in 75 mL of ethanol was heated at reflux for about five hours. The reaction mixture was then concentrated under reduced pressure to a residue, which was taken up in ethyl acetate and washed with aqueous solutions saturated with sodium bicarbonate and sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. NMR analysis of the residue indicated the presence of product and acetic acid. The residue was washed with several portions of an aqueous solution saturated with sodium bicarbonate, and then was extracted thoroughly with ethyl acetate. The combined extracts were dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 2.0 grams of 2-(2-methylpropylamino)-4-ethoxycarbonylamino-5-fluoroaniline.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for about five hours
  3. concentrationThe reaction mixture was then concentrated under reduced pressure to a residue, which
  4. washwashed with aqueous solutions saturated with sodium bicarbonate and sodium chloride
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure to a residue
  8. washThe residue was washed with several portions of an aqueous solution saturated with sodium bicarbonate
  9. extractionwas extracted thoroughly with ethyl acetate
  10. dry with materialThe combined extracts were dried with sodium sulfate
  11. filtrationfiltered
  12. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0225dc19c90c4b84b11be43618ca4a2d
Source dataset
uspto-grants-1997_08
Patent number
US05661108

Reaction notes

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