HCID 68006026, compound → HCID 68006335, compound

HRID 1026532Notes

Reaction equation

HRID 1026532 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:19]([O-])=O)[C:5]([O:8][C:9]2([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:11][CH2:10]2)=[N:6][CH:7]=1>[Fe].C(O)(=O)C>[NH2:19][C:4]1[C:5]([O:8][C:9]2([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:11][CH2:10]2)=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 1

HCID 68006026HCID 68006026, compound

Product 1

HCID 68006335HCID 68006335, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

At room temperature, to an acetic acid solution (100 ml) of tert-butyl 1-[(5-chloro-3-nitropyridin-2-yl)oxy]cyclopropanecarboxylate (9.61 g) was added iron powder (13.6 g), and stirred for 7 hours, followed by concentration under reduced pressure. To the residue were added ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution for neutralization, followed by filtration through Celite. The organic layer separated from the filtrate was washed with saturated sodium chloride solution, and the aqueous layer was collected and extracted with ethyl acetate. The collected organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford tert-butyl 1-[(3-amino-5-chloropyridin-2-yl)oxy]cyclopropanecarboxylate (7.88 g).

Workup

  1. concentrationfollowed by concentration under reduced pressure
  2. additionTo the residue were added ethyl acetate
  3. filtrationa saturated aqueous sodium hydrogen carbonate solution for neutralization, followed by filtration through Celite
  4. customThe organic layer separated from the filtrate
  5. washwas washed with saturated sodium chloride solution
  6. customthe aqueous layer was collected
  7. extractionextracted with ethyl acetate
  8. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-69274d7be4dc4280a9b30e6ed99143b9
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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