HCID 14368366, compound → HCID 14368376, compound

HRID 1762212Notes

Reaction equation

HRID 1762212 reaction equation
C([O:3][C:4]([C:6]1[CH:26]=[CH:25][C:9]([CH2:10][O:11][C:12]2[C:13]3[N:14]([C:18]([CH2:22][C:23]#[CH:24])=[C:19]([CH3:21])[N:20]=3)[CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:7]=1)=[O:5])C>C(O)C.S(=O)(=O)(O)O>[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:10][O:11][C:12]2[C:13]3[N:14]([C:18]([CH2:22][C:23]#[CH:24])=[C:19]([CH3:21])[N:20]=3)[CH:15]=[CH:16][CH:17]=2)=[CH:25][CH:26]=1)([OH:5])=[O:3]

Participants

4

Reactant 1

HCID 14368366HCID 14368366, compound

Product 1

HCID 14368376HCID 14368376, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 8-(4-ethoxycarbonylbenzyloxy)-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine (1.04 g) in ethanol (15 ml) and 20% sulfuric acid (40 ml) was refluxed for 5 hours and then ethanol was evaporated in vacuo. The mixture was cooled and the resulting precipitates were collected by filtration. The obtained sulfate was treated with an aqueous solution of sodium bicarbonate and then the mixture was adjusted to pH 4.5 with acetic acid. The resulting precipitates were collected by filtration and air-dried to give 8-(4-carboxybenzyloxy)-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine (0.66 g).

Workup

  1. temperaturewas refluxed for 5 hours
  2. customethanol was evaporated in vacuo
  3. temperatureThe mixture was cooled
  4. customthe resulting precipitates
  5. filtrationwere collected by filtration
  6. additionThe obtained sulfate was treated with an aqueous solution of sodium bicarbonate
  7. customThe resulting precipitates
  8. filtrationwere collected by filtration
  9. customair-dried

Sources & evidence

ORD record
ord-7e7586660254438192dc790606c0401e
Source dataset
uspto-grants-1989_05
Patent number
US04831041

Reaction notes

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