Ethyl Acetate → HCID 86675400, compound

HRID 407209Notes

Reaction equation

HRID 407209 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[O:13][CH3:14].[N-:15]=[N+]=[N-].[Na+].CCOC(C)=O.[BH4-].[Na+]>CN(C)C=O.O>[NH2:15][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:3]=1[O:13][CH3:14]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 4311764Sodium borohydrideHCID 73554912HCID 73554912, compound

Product 1

HCID 86675400HCID 86675400, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 4,6-dichloro-3-methoxypicolinate (320 mg, 1.4 mmol) was dissolved in dry N,N-dimethylformamide (DMF; 5 mL), treated with sodium azide (130 mg, 2.0 mmol) and heated at 50° C. for 5 h. After cooling, the mixture was shaken with EtOAc (20 mL) and H2O (10 mL). The organic phase was washed with H2O (2×10 mL) and satd aq NaCl (1×10 mL), dried (Na2SO4) and evaporated. This material was dissolved in methyl alcohol (CH3OH; 15 mL), treated with sodium borohydride (NaBH4; 55 mg, 1.4 mmol) and stirred at 20° C. for 1 h. The mixture was treated with H2O (10 mL), and the volatiles were removed under vacuum. The residue was taken up in EtOAc (25 mL), washed with H2O (10 mL) and satd aq sodium chloride (NaCl; 10 mL), dried (Na2SO4), and evaporated to give the desired product as a white solid (100 mg, 33%): mp 78-79° C.; 1H NMR (400 MHz, CDCl3) δ 6.76 (s, 1H), 4.84 (s, 2H), 3.95 (s, 3H), 3.87 (s, 3H); EIMS m/z 216.

Workup

  1. temperatureAfter cooling
  2. washThe organic phase was washed with H2O (2×10 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. dissolutionThis material was dissolved in methyl alcohol (CH3OH; 15 mL)
  6. customthe volatiles were removed under vacuum
  7. washwashed with H2O (10 mL)
  8. dry with materialdried (Na2SO4)
  9. customevaporated

Sources & evidence

ORD record
ord-3910ec67d399448cb4be16eb54e6b0e3
Source dataset
uspto-grants-2014_06
Patent number
US08754229B2

Reaction notes

Loading…