Pyridine → HCID 54076611, compound

HRID 1418741Notes

Reaction equation

HRID 1418741 reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[C:13](Cl)(Cl)=[O:14].Cl.[CH3:18][O:19][C:20](=[O:23])[CH2:21][NH2:22].N1C=CC=CC=1>O1CCCC1.N.O>[CH3:18][O:19][C:20](=[O:23])[CH2:21][NH:22][C:13](=[O:14])[NH:6][C:5]1[CH:7]=[C:8]([F:9])[C:2]([F:1])=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

8

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 122755Glycine methyl ester hydrochlorideHCID 1571514,5-Difluoro-2-nitroaniline

Product 1

HCID 54076611HCID 54076611, compound

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,5-difluoro-2-nitroaniline (1.07 g, 6.15 mmol) in tetrahydrofuran is cooled to 2° C., treated with phosgene (3.8 mL, 1.93M, 7.33 mmol), stirred at ice-bath temperature for 2 hours, treated with glycine methyl ester hydrochloride (1.02 g, 8.12 mmol), treated with pyridine (1 mL, 12.64 mmol), stirred at room temperature for 3 days, diluted with concentrated ammonia solution and water, and extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a residue. Column chromatography of the residue using silica gel and an ethyl acetate/hexanes (1:3) solution gives the title product as a solid, mp 118.9°-122.9° C.

Workup

  1. stirringstirred at room temperature for 3 days
  2. extractionextracted with ethyl acetate
  3. washwashed sequentially with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a residue

Sources & evidence

ORD record
ord-a2c1bd85c0264fe5ad2a86f432cd93c5
Source dataset
uspto-grants-1999_03
Patent number
US05883282

Reaction notes

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