Ethyl Acetate → HCID 21696602, compound

HRID 378800Notes

Reaction equation

HRID 378800 reaction equation
C[C:2]1[C:3](Cl)=[C:4]([Cl:20])C(C(O)=O)=[N:6][C:7]=1[O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=1.[N-:22]=[N+]=[N-].[Na+].[BH4-].[Na+].[C:28]([O:31][CH2:32]C)(=[O:30])[CH3:29]>CN(C=O)C.O>[NH2:22][C:3]1[CH:2]=[C:7]([O:8][C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=2)[N:6]=[C:29]([C:28]([O:31][CH3:32])=[O:30])[C:4]=1[Cl:20]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 4311764Sodium borohydrideHCID 21696632HCID 21696632, compound

Product 1

HCID 21696602HCID 21696602, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 3,4-dichloro-6-(3,5-dichlorophenoxy)pyridine-2-carboxylic acid (1.93 g, 5.26 mmol) was dissolved in a minimum amount of DMF and to it was carefully added NaN3 (0.444 g, 6.84 mmol) and water to form a homogeneous mixture which was heated to 70° C. and stirred overnight. The reaction mixture was poured into a water-ice mixture and the product was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with pet ether/water (200 mL), dried (MgSO4) and concentrated to dryness in vacuo. The resulting oil was dissolved in methanol and to it was added NaBH4 (0.200 g, 5.26 mmol) and stirred at RT for 1.5 hr. Ethyl acetate and water was added and the aqueous phase was extracted with ethyl acetate (2×100 mL). The combined extracts were dried (MgSO4) and concentrated to dryness. Purification by column chromatography (silica gel) using an eluent of 20% diethyl ether/hexane-50% diethyl ether/hexane to give 0.900 g of clear solid.

Workup

  1. customto form a homogeneous mixture which
  2. extractionthe product was extracted with ethyl acetate (3×100 mL)
  3. washThe combined extracts were washed with pet ether/water (200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to dryness in vacuo
  6. dissolutionThe resulting oil was dissolved in methanol and to it
  7. stirringstirred at RT for 1.5 hr
  8. extractionthe aqueous phase was extracted with ethyl acetate (2×100 mL)
  9. dry with materialThe combined extracts were dried (MgSO4)
  10. concentrationconcentrated to dryness
  11. customPurification by column chromatography (silica gel)

Sources & evidence

ORD record
ord-40a76c9565cb4ee5a176d2c875d6f325
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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