HCID 11299248, compound → HCID 10888757, compound

HRID 1004074Notes

Reaction equation

HRID 1004074 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10](C(=O)C)[CH2:9][CH2:8]2>Cl>[CH3:1][O:2][C:3](=[O:17])[CH2:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH2:9][CH2:8]2

Participants

3

Reactant 1

HCID 11299248HCID 11299248, compound

Product 1

HCID 10888757HCID 10888757, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of (1-acetyl-2,3-dihydro-1H-indol-5-yl)-acetic acid methyl ester (0.60 g) in 2M hydrochloric acid (15 ml) was heated under reflux for 5 h. The mixture was evaporated to dryness. The residue was dissolved in methanol (20 ml) and treated with concentrated sulphuric acid (5 drops). The solution was stirred at room temperature for one hour, then concentrated. The residue was partitioned between ethyl acetate and sodium carbonate solution. The organic phase was dried and evaporated and the residue purified by chromatography eluting with cyclohexane:ethyl acetate (2:1) to give the title compound as a brown oil (0.40 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 h
  3. customThe mixture was evaporated to dryness
  4. dissolutionThe residue was dissolved in methanol (20 ml)
  5. additiontreated with concentrated sulphuric acid (5 drops)
  6. concentrationconcentrated
  7. customThe residue was partitioned between ethyl acetate and sodium carbonate solution
  8. customThe organic phase was dried
  9. customevaporated
  10. customthe residue purified by chromatography
  11. washeluting with cyclohexane:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-84ddd957141d440299ff9637e83c5fd5
Source dataset
uspto-grants-2000_04
Patent number
US06048872

Reaction notes

Loading…