Reaction #159843

Reaction equation

methyl 2-((5-methoxy-6-nitropyridin-2-yl)methylthio)acetate

→

2-((5-methoxy-6-nitropyridin-2-yl)methylthio)acetic acid

Yield 97.0%

Solvents

sodium carbonate

Conditions

Workup

1. 1
   Otherthe mixture was reacted at 50° C. for 16 hrs
2. 2
   OtherThe mixture was evaporated in vacuo

Procedure

To 150 mL of sodium carbonate 1N solution, methyl 2-((5-methoxy-6-nitropyridin-2-yl)methylthio)acetate (10 mmol, 2.72 g) was added and the mixture was reacted at 50° C. for 16 hrs. The mixture was evaporated in vacuo to give 2-((5-methoxy-6-nitropyridin-2-yl)methylthio)acetic acid. Yield 97%; m.p. 239-230° C. (dec); 1H-NMR (D2O) δ: 3.04 (s, 2H, CH2), 3.65 (s, 2H, CH2), 3.78 (s, 3H, OCH3), 7.54 (d, 1H, J=8.4 Hz, Py-H), 8.429 (d, 1H, J=8.4 Hz, Py-H); 13C-NMR (O2O) δ: 35.79, 36.48, 56.96, 125.75, 130.76, 145.07, 147.96, 148.14, 177.11; DEPT-135 (D2O) δ: 35.79 (CH2), 36.48 (CH2), 56.96 (CH3), 125.75 (CH), 130.76 (CH); HR-MS (ESI+) m/z 257.0101 [M−H]−, C9H10N2O5S requires 258.0310.

Source