Acetic Acid → HCID 90403969, compound

HRID 1468975Notes

Reaction equation

HRID 1468975 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:16]=[CH:15][C:11]3=[N:12][O:13][N:14]=[C:10]3[C:9]=2F)[N:5]=[C:4]([C:18]([O:20][CH3:21])=[O:19])[C:3]=1[Cl:22].C[O-].[Na+].[C:26](O)(=[O:28])C>CO>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:16]=[CH:15][C:11]3=[N:12][O:13][N:14]=[C:10]3[C:9]=2[O:28][CH3:26])[N:5]=[C:4]([C:18]([O:20][CH3:21])=[O:19])[C:3]=1[Cl:22]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium Methoxide2×HCID 90403438HCID 90403438, compound

Product 1

HCID 90403969HCID 90403969, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
20 °C

Procedure

Methyl 4-amino-3-chloro-6-(4-fluorobenzo[c][1,2,5]oxadiazol-5-yl)picolinate (70 mg, 0.21 mmol) was dissolved in 2 mL dry methanol, treated with 0.20 mL 30% sodium methoxide solution in methanol and stirred for 90 min at 20° C. The excess sodium methoxide was neutralized by addition of acetic acid and the volatiles were removed by rotary evaporation. The residue was taken up in 10 mL ethyl acetate, washed with 2 mL saturated NaHCO3, 2 mL saturated NaCl, dried (Na2SO4) and evaporated to give the title compound as white solid (51 mg, 72%): mp 142-144° C.; 1H NMR (400 MHz, CDCl3) δ 8.01 (d, J=9.3 Hz, 1H), 7.51 (d, J=9.3 Hz, 1H), 7.44 (s, 1H), 4.86 (s, 2H), 4.39 (s, 3H), 4.00 (s, 3H); ESIMS m/z 335 ([M+H]+), 333 ([M−H]−).

Workup

  1. customthe volatiles were removed by rotary evaporation
  2. washwashed with 2 mL saturated NaHCO3, 2 mL saturated NaCl
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-afde3076655241a093cfb982dc237c17
Source dataset
uspto-grants-2015_04
Patent number
US09006250B2

Reaction notes

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