Methanol → Methyl 2-hydroxy-5-nitronicotinate

HRID 347566Notes

Reaction equation

HRID 347566 reaction equation
[OH:1][C:2]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:18]O>>[N+:11]([C:8]1[CH:7]=[C:3]([C:4]([O:6][CH3:18])=[O:5])[C:2](=[O:1])[NH:10][CH:9]=1)([O-:13])=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178524577HCID 178524577, compound

Product 1

HCID 7204882Methyl 2-hydroxy-5-nitronicotinateYield 99%

Conditions

Temperature
0 °C

Procedure

To a solution of 2-hydroxy-5-nitronicotinic acid (0.80 g, 4.35 mmol, Combi-Blocks) in methanol (10 mL) at 0° C. was added thionyl chloride (1 mL) dropwise. The mixture was stirred at 0° C. for 1 h, then at 60° C. for 2 h. The excess methanol was removed under reduced pressure and the residue was neutralized with aqueous sodium bicarbonate solution. The solid was collected, washed with water and dried to afford the title compound (0.85 g, 99%). 1H NMR (DMSO-d6) δ 8.44 (s, 1H), 8.34 (s, 1H), 3.67 (s, 3H); MS(ESI+) m/z 199 (M+H)+.

Workup

  1. waitat 60° C. for 2 h
  2. customThe excess methanol was removed under reduced pressure
  3. customThe solid was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-281336b64d834499a705e3fa855701c0
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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