Nitric Acid → 2-Methyl-1-nitroindolizine

HRID 502479Notes

Reaction equation

HRID 502479 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[CH:7]=[C:8]2[N:13]([CH:14]=1)[CH:12]=[CH:11][CH:10]=[CH:9]2>S(=O)(=O)(O)O>[CH3:5][C:6]1[C:7]([N+:1]([O-:4])=[O:2])=[C:8]2[N:13]([CH:14]=1)[CH:12]=[CH:11][CH:10]=[CH:9]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 5826302-Methylindolizine

Product 1

HCID 6006432-Methyl-1-nitroindolizine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Nitric acid (5 mL, 70%) was added slowly to a stirred solution of 2-methylindolizine 1 (see preparation of Example 1) (5 g, 38.2 mmol) in concentrated sulphuric acid (15 mL, 96%) at 0° C. After 5 minutes, the brown solution obtained was poured onto crushed ice. The orange precipitate formed was immediately isolated by filtration, washed with copious amounts of water and then dried under vacuum in the presence of P2O5 for a night to give 2-methyl-1-nitroindolizine 13 (3 g), m.p. 137-139° C. 1H NMR (DMSO-d6): δ 8.55 (dt, J=6.7, 1.0 Hz, 1H), 8.20 (d, J=9.1 Hz, 1H), 7.54-7.48 (m, 2H), 7.11 (dt, J=8.0, 1.2 Hz, 1H), 2.47 (d, J=1.0 Hz, 3H). 13C NMR (DMSO-d6): δ 132.2, 128.0, 127.7, 123.0, 122.8, 117.8, 115.0, 114.7, 12.4.

Workup

  1. customthe brown solution obtained
  2. additionwas poured
  3. customonto crushed ice
  4. customThe orange precipitate formed
  5. customwas immediately isolated by filtration
  6. washwashed with copious amounts of water
  7. dry with materialdried under vacuum in the presence of P2O5 for a night

Sources & evidence

ORD record
ord-7693f606e82d451a8bc7bc8ddf4dd686
Source dataset
uspto-grants-2010_08
Patent number
US07776107B2

Reaction notes

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