Hydrochloric Acid → HCID 67328970, compound

HRID 1023351Notes

Reaction equation

HRID 1023351 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:18]=[CH:19]/[C:20]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=1.[Sn].Cl.[OH-].[Na+]>CCO>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:7]2[CH:6]=[CH:5][C:4](/[CH:18]=[CH:19]/[C:20]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:21])=[CH:3][C:2]=2[Cl:1])=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5352426Tin atomHCID 67327396HCID 67327396, compound

Product 1

HCID 67328970HCID 67328970, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an EtOH (500 mL) solution of butyl (E)-3-{3-chloro-4-[(5-nitropyridin-2-yl)oxy]phenyl}prop-2-enoate (45.4 g) and tin powder (57.3 g) was slowly added conc. HCl (36.6 mL) at 0° C., then the resultant mixture was stirred at room temperature for 1 hour. The reaction mixture was neutralized with 5 M aqueous NaOH, and the mixture was filtered off on Celite. The filtrate was evaporated and water was added to the residue, and the mixture was extracted with AcOEt. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1) to afford butyl (E)-3-{4-[(5-amino-pyridin-2-yl)oxy]-3-chlorophenyl}prop-2-enoate (39.9 g) as a pale yellow solid.

Workup

  1. customat 0° C.
  2. filtrationthe mixture was filtered off on Celite
  3. customThe filtrate was evaporated
  4. additionwater was added to the residue
  5. extractionthe mixture was extracted with AcOEt
  6. washThe organic layer was washed with water and saturated aqueous NaCl
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1)

Sources & evidence

ORD record
ord-bf231b32ef564681a87b59eeca622712
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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