Nitric Acid → N-(4-chloro-2-fluoro-5-nitrophenyl)acetamide

HRID 2292223Notes

Reaction equation

HRID 2292223 reaction equation
S(=O)(=O)(O)O.[C:6]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[F:17])(=[O:8])[CH3:7].[N+:18]([O-])([OH:20])=[O:19]>>[C:6]([NH:9][C:10]1[C:11]([F:17])=[CH:12][C:13]([Cl:16])=[C:14]([N+:18]([O-:20])=[O:19])[CH:15]=1)(=[O:8])[CH3:7]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 8531744'-Chloro-2'-fluoroacetanilide

Product 1

HCID 13563753N-(4-chloro-2-fluoro-5-nitrophenyl)acetamideYield 99.5%

Procedure

To 20% ice-cooled fuming sulfuric acid (50 g), 4-(N-acetylamino)-1-chloro-3-fluorobenzene (9.4 g) was dissolved, followed by gradual addition of fuming nitric acid (3.5 g) while keeping the temperature at 0° to 5° C. The resultant mixture was stirred at the same temperature for 1 hour and poured into ice (50 g). The precipitate crystals were collected by filteration, and the filtrate was washed with water and dried to give 11.6 g of 4-(N-acetylamino)-1-chloro-5-fluoro-2-nitrobenzene. M.P., 124.7°-125.7° C.

Workup

  1. dissolutionwas dissolved
  2. customat 0° to 5° C
  3. customThe precipitate crystals were collected by filteration
  4. washthe filtrate was washed with water
  5. customdried

Sources & evidence

ORD record
ord-f93d2934c89840fa83a59c8bb918bbdf
Source dataset
uspto-grants-1989_01
Patent number
US04801408

Reaction notes

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