Nitric Acid → HCID 21190112, compound

HRID 619525Notes

Reaction equation

HRID 619525 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]2[CH:12]=[C:13]([CH3:15])[N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:2].[N+:16]([O-])([OH:18])=[O:17].[OH-].[Na+]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4]([C:6]1[N:11]2[C:12]([N+:16]([O-:18])=[O:17])=[C:13]([CH3:15])[N:14]=[C:10]2[CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 11148398HCID 11148398, compound

Product 1

HCID 21190112HCID 21190112, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 1.02 g (5.0 mmol) of 5-ethoxycarbonyl-2-methyl-imidazo[1,2-a]pyridine in 2.5 ml of conc. sulfuric acid was added dropwise, while stirring under ice-cooling, 2.0 ml of conc. nitric acid. The mixture was stirred for 10 minutes at the same temperature. The reaction mixture was poured into ice-water, whose pH was adjusted to 3-with a 10% aqueous solution of NaOH. The resulting crystalline precipitates were collected by filtration, washed with water and dried, followed by further purification by column chromatography (eluent: ethyl acetate) to afford 752 mg of the desired compound (60.4%, a yellow solid).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred for 10 minutes at the same temperature
  3. customThe resulting crystalline precipitates
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customdried
  7. customfollowed by further purification by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-1106e5f3ef0d42628446ddb3620289de
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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