Methanol → HCID 58017108, compound

HRID 883663Notes

Reaction equation

HRID 883663 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:6](=[O:16])[C:5]2([CH:19](C#N)[C:20]([O:22]C)=O)[C:17]#[N:18].C[OH:27]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]3([CH2:19][C:20](=[O:22])[NH:18][C:17]3=[O:27])[C:6](=[O:16])[N:7]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:8]2=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 68185069HCID 68185069, compound

Product 1

HCID 58017108HCID 58017108, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of methyl [5-chloro-3-cyano-1-(2-methoxy-2-oxoethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl](cyano)acetate, intermediate 46, (10.56 g, 29.19 mmol) in dry methanol (190 ml) was purged with hydrogen chloride at −78° C. for 45 minutes. The suspension was allowed to warm up to ambient temperature and further heated up to reflux for 4 hours. The solvent was removed in vacuo, the remaining solid was suspended in glacial acetic acid (300 ml) and heated up to reflux for 5 hours. Evaporation under reduced pressure gave a red-brown oil, which was redissolved in ethyl acetate (300 ml). The solution was washed with water (2×200 ml), the aqueous washes were once back-extrated with ethyl acetate (200 ml) and the organic extracts were dried (MgSO4) to give the title compound (10.87 g, quant.) as solidified foam (HPLC purity: 91%). MS (ESI+): 323.2; MS (ESI−): 321.1

Workup

  1. customwas purged with hydrogen chloride at −78° C. for 45 minutes
  2. temperaturefurther heated up
  3. temperatureto reflux for 4 hours
  4. customThe solvent was removed in vacuo
  5. temperatureheated up
  6. temperatureto reflux for 5 hours
  7. customEvaporation under reduced pressure
  8. customgave a red-brown oil, which
  9. washThe solution was washed with water (2×200 ml)
  10. dry with materialthe organic extracts were dried (MgSO4)

Sources & evidence

ORD record
ord-1fb2d84dca8a4f8db982c4adfe551baf
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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