Ammonia → 4-Fluoro-3-nitroaniline

HRID 267836Notes

Reaction equation

HRID 267836 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.OS(O)(=O)=O.[N+:14]([O-])([OH:16])=[O:15].N>>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 97314-Fluoroaniline

Product 1

HCID 677684-Fluoro-3-nitroaniline

Conditions

Temperature
5 °C

Procedure

To a solution of 139 g. of p-fluoroaniline in 834 g. of H2SO4, 100%, a mixture of 81.3 g. of HNO3, 100% in 489 g. H2SO4, 100%, is slowly added at 8°-10°C. One hour after this addition, the mixture is poured on 800 g. of ice and the resulting solution made alkaline with 2300 ml. of conc. aqua ammonia. On cooling to approxiamtely 5°C., the orange crude product is filtered off, sharply sucked off, and stirred with 600 ml. of water and 120 ml. of conc. HCl at room temperature. The insoluble, dark-brown solid is filtered off, the filtrate made alkaline with 82 g. of solid sodium carbonate, and the solid filtered off and dried in vacuo at 60°-70°C or in the air.

Workup

  1. additionOne hour after this addition
  2. additionthe mixture is poured on 800 g
  3. filtrationthe orange crude product is filtered off
  4. customat room temperature
  5. filtrationThe insoluble, dark-brown solid is filtered off
  6. filtrationof solid sodium carbonate, and the solid filtered off
  7. customdried in vacuo at 60°-70°C or in the air

Sources & evidence

ORD record
ord-b6eac4e39b704f7a9b00eaad16e053aa
Source dataset
uspto-grants-1976_03
Patent number
US03944612

Reaction notes

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