Sodium Carbonate → 3-Iodo-2-methyl-5-nitropyridine

HRID 77731Notes

Reaction equation

HRID 77731 reaction equation
[I:1][C:2]1[C:3]([CH:11](C(OCC)=O)C(OCC)=O)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.C([O-])([O-])=O.[Na+].[Na+]>S(=O)(=O)(O)O>[I:1][C:2]1[C:3]([CH3:11])=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 59776929Diethyl (3-iodo-5-nitropyridin-2-yl)malonate

Product 1

HCID 591983253-Iodo-2-methyl-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Diethyl (3-iodo-5-nitropyridin-2-yl)malonate (0.250 g, 0.000612 mol) was heated in 6 M sulfuric acid (3 mL) at 100° C. for 16 hours. The reaction was neutralized with solid Na2CO3, extracted with EtOAc and the organic extracts were washed with water, saturated NaCl, dried (MgSO4) and stripped in vacuo. NMR analysis indicated that it was clean enough for the next reaction. 1H NMR (400 MHZ, CDCl3): δ 9.27 (d, 1H), 8.82 (d, 1H), 2.87 (s, 3H); MS (ES) (M+H)=265.

Workup

  1. extractionextracted with EtOAc
  2. washthe organic extracts were washed with water, saturated NaCl
  3. dry with materialdried (MgSO4)
  4. customwas clean enough for the next reaction

Sources & evidence

ORD record
ord-b2b834e8ae7f449d8368a7933a6f338c
Source dataset
uspto-grants-2014_09
Patent number
US08841318B2

Reaction notes

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