Acetic Acid → HCID 178424435, compound

HRID 2299265Notes

Reaction equation

HRID 2299265 reaction equation
[NH2:1][C:2]1[C:3]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])=[C:4]2[N:9]([C:10]=1[C:11]#[N:12])[CH:8]=[CH:7][CH:6]=[CH:5]2.[C:22](OC(=O)C)(=O)[CH3:23].C(O)(=[O:31])C>>[OH:31][C:11]1[C:10]2[N:9]3[C:4]([CH:5]=[CH:6][CH:7]=[CH:8]3)=[C:3]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:2]=2[N:1]=[C:22]([CH3:23])[N:12]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 22034110HCID 22034110, compound

Product 1

HCID 178424435HCID 178424435, compound

Procedure

A solution of 2-amino-3-cyano-1-(2,4,6-trimethylphenyl)indolizine (220 mg) in an acetic anhydride (0.5 mL)—acetic acid (2 mL) mixture is heated at 100° C. for 1 hour. The mixture is cooled to room temperature and concentrated in vacuo. The residue is then heated in 85% phosphoric acid (5 mL) at 100° C. for 1.5 hours, allowed to cool to room temperature, diluted with water, and neutralized to pH 7 by adding aqueous ammonium hydroxide. The resulting yellow suspension is extracted twice with dichloromethane and the combined extracts are dried (Na2SO4), filtered, concentrated, and chromatographed (50% ethyl acetate in hexane to 10% methanol in ethyl acetate) to give 120 mg of the title compound as a yellow solid.

Workup

  1. concentrationconcentrated in vacuo
  2. temperatureThe residue is then heated in 85% phosphoric acid (5 mL) at 100° C. for 1.5 hours
  3. temperatureto cool to room temperature
  4. additiondiluted with water
  5. additionneutralized to pH 7 by adding aqueous ammonium hydroxide
  6. extractionThe resulting yellow suspension is extracted twice with dichloromethane
  7. dry with materialthe combined extracts are dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customchromatographed (50% ethyl acetate in hexane to 10% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-8fef9663bb204bf783c24c7e5cbc3f9d
Source dataset
uspto-grants-2002_12
Patent number
US06495686B2

Reaction notes

Loading…