HCID 68808604, compound → HCID 68810234, compound

HRID 1782619Notes

Reaction equation

HRID 1782619 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([N+:14]([O-])=O)[C:11]([Cl:17])=[CH:10][C:9]=2[F:18])[N:5]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[C:3]=1[Cl:23]>C(O)(=O)C.[Fe]>[CH3:22][O:21][C:19]([C:4]1[C:3]([Cl:23])=[C:2]([NH2:1])[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([NH2:14])[C:11]([Cl:17])=[CH:10][C:9]=2[F:18])[N:5]=1)=[O:20]

Participants

4

Reactant 1

HCID 68808604HCID 68808604, compound

Product 1

HCID 68810234HCID 68810234, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
85 °C

Procedure

Iron powder (0.78 g, 13.9 mmol) was added to a slurry of methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-5-nitrophenyl)pyridine-2-carboxylate (0.5 g, 1.39 mmol) in acetic acid (20 mL) in a 100 mL round bottomed flask. The mixture was heated to 85° C. for 15 minutes. then cooled to room temperature and filtered through celite with ethanol and the filtrate concentrated in vacuo. The residue was partitioned between ethyl acetate and saturated NaHCO3, the layers separated, the aqueous phase extracted with ethyl acetate and the combined organics dried (Na2SO4). Filtration and concentration gave 4-amino-3-chloro-6-(5-amino-4-chloro-2-fluorophenyl)pyridine-2-carboxylic acid methyl ester (0.44 g, 1.33 mmol) as a light brown solid: mp 99-101° C.

Workup

  1. temperaturethen cooled to room temperature
  2. filtrationfiltered through celite with ethanol
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate and saturated NaHCO3
  5. customthe layers separated
  6. extractionthe aqueous phase extracted with ethyl acetate
  7. dry with materialthe combined organics dried (Na2SO4)
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-b5cfacbfd659408caba2c0154e739c11
Source dataset
uspto-grants-2009_03
Patent number
US07498468B2

Reaction notes

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