Phosphorus oxychloride → HCID 21906257, compound

HRID 1793802Notes

Reaction equation

HRID 1793802 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]([OH:9])=O.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:7]([C:6]2[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[N+:11]([O-:13])=[O:12])=[O:9])=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 661742-Amino-5-chloropyridineHCID 27374205-Fluoro-2-nitrobenzoic acid

Product 1

HCID 21906257HCID 21906257, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 5-fluoro-2-nitrobenzoic acid (10.0 g, 54 mmol, 1.0 equiv.), 2-amino-5-chloropyridine (9.02 g, 1.3 equiv.), in 80 mL of pyridine was treated with phosphorous oxychloride (25.3 g, 3.0 equiv.) for 30 minutes. The volatile was evaporated and the residue was redissolved into EtOAc, washed with 1N HCl, saturated aqueous NaHCO3 and saturated aqueous NaCl. The organic layer was dried over Na2SO4, filtered, and evaporated. The product was triturated with diethyl ether to give N-(5-chloro-2-pyridinyl)-(2-nitro)-5-fluorophenylcarboxamide (11.5 g, 72%). MS found for C12H7ClFN3O'(M+H)+: 296, (M+2+H): 298.

Workup

  1. customThe volatile was evaporated
  2. dissolutionthe residue was redissolved into EtOAc
  3. washwashed with 1N HCl, saturated aqueous NaHCO3 and saturated aqueous NaCl
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was triturated with diethyl ether

Sources & evidence

ORD record
ord-14264308875c496eb5454edb75c702cc
Source dataset
uspto-grants-2006_04
Patent number
US07022695B2

Reaction notes

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