Hydrochloric Acid → 4-Fluoro-2-methyl-6-nitroaniline

HRID 52651Notes

Reaction equation

HRID 52651 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:15])[C:5]([NH:11]C(C)=O)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.Cl.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH3:15])[C:5]([NH2:11])=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54330341N-(4-fluoro-2-methyl-6-nitrophenyl)acetamide

Product 1

HCID 103748424-Fluoro-2-methyl-6-nitroanilineYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 22.4 grams (0.106 mole) of 5-fluoro-2-methylcarbonylamino-3-methylnitrobenzene, 100 mL of concentrated hydrochloric acid, and 100 mL of ethanol was heated at reflux for about 17 hours. The reaction mixture was cooled and poured into 500 grams of ice. The mixture was made basic with aqueous 50% sodium hydroxide. The resultant solid was collected by filtration and was thoroughly washed with water. The solid was dried at about 60° C. under vacuum, yielding 17.0 grams of 4-fluoro-2-nitro-6-methylaniline, mp 111°-113° C. The NMR spectrum was consistent with the proposed structure. The reaction was repeated to obtain more product.

Workup

  1. temperatureat reflux for about 17 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe resultant solid was collected by filtration
  4. washwas thoroughly washed with water
  5. customThe solid was dried at about 60° C. under vacuum

Sources & evidence

ORD record
ord-68071ff8562a46d1ad8c90a9acf94b0f
Source dataset
uspto-grants-1997_04
Patent number
US05616718

Reaction notes

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