Ammonium Hydroxide → 5-Fluoro-2-nitrobenzamide

HRID 1640964Notes

Reaction equation

HRID 1640964 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].S(Cl)(Cl)=O.[NH4+:18].[OH-]>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([NH2:18])=[O:8]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 27374205-Fluoro-2-nitrobenzoic acid

Product 1

HCID 186681655-Fluoro-2-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-Fluoro-2-nitro-benzoic acid (17.9 g, 96.8 mmol) was heated in thionyl chloride (35 mL, 5 mol eq.) for two hours at 85° C. (oil bath temperature). The reaction mixture was evaporated, taken up and evaporated twice with dry toluene. The resulting acid chloride was dissolved in dry dioxane (180 mL) and added to an ice-water bath cooled solution of 33% NH4OH (23.5 mL, 2 mol eq.) in dioxane (180 mL). The reaction was allowed to warm up gradually to room temperature and then evaporated to dryness. The crystalline residue was triturated in water (50 mL), collected by filtration, washed with a small amount of water and dried in vacuo at 80° C. to constant weight (17.56 g, 98.5%).

Workup

  1. customThe reaction mixture was evaporated
  2. customevaporated twice with dry toluene
  3. dissolutionThe resulting acid chloride was dissolved in dry dioxane (180 mL)
  4. additionadded to an ice-water bath
  5. customevaporated to dryness
  6. customThe crystalline residue was triturated in water (50 mL)
  7. filtrationcollected by filtration
  8. washwashed with a small amount of water
  9. customdried in vacuo at 80° C. to constant weight (17.56 g, 98.5%)

Sources & evidence

ORD record
ord-1ce05c996f7b421bb8c9d57872e208aa
Source dataset
uspto-grants-2012_02
Patent number
US08114865B2

Reaction notes

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