Nitric Acid → 4-Iodo-5-nitro-2,3-dihydrofuro[2,3-b]pyridine

HRID 1499423Notes

Reaction equation

HRID 1499423 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[I:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]2[O:17][CH2:18][CH2:19][C:12]=12>>[I:10][C:11]1[C:16]([N+:1]([O-:4])=[O:2])=[CH:15][N:14]=[C:13]2[O:17][CH2:18][CH2:19][C:12]=12

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 867266744-iodo-2H,3H-furo(2,3-b)pyridine

Product 1

HCID 867266754-Iodo-5-nitro-2,3-dihydrofuro[2,3-b]pyridineYield 92%

Procedure

A solution of fuming nitric acid (15.0 mL, 358 mmol) in concentrated sulfuric acid (15.0 mL, 281 mmol) was added slowly over a period of 15 min. to a stirred solution of 4-iodo-2,3-dihydrofuro[2,3-b]pyridine (2.237 g, 9.055 mmol) in sulfuric acid (10.0 mL, 188 mmol) at −10° C. The reaction mixture was allowed to warm to room temperature, and stirred for a further 16 h. The reaction mixture was quenched by pouring onto crushed ice and was then extracted with EtOAc (6×100 mL). The organic extracts were combined and washed with saturated aq. NaHCO3 (2×300 mL) and brine (300 mL), then dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes) to give the sub-title compound as a pale yellow solid (2.43 g, 92%). LCMS calc. for C2H61N2O3 (M+H)+: m/z=292.9. found 293.0.

Workup

  1. customThe reaction mixture was quenched
  2. additionby pouring
  3. customonto crushed ice
  4. extractionwas then extracted with EtOAc (6×100 mL)
  5. washwashed with saturated aq. NaHCO3 (2×300 mL) and brine (300 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-02a6d1c464e94074b8ba0826ca979736
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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