Ethanol → HCID 86731081, compound

HRID 1844412Notes

Reaction equation

HRID 1844412 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[C:3]1=[O:12].C(O)C.[N+](=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N-]>CN(C=O)C>[OH:11][C:4]1[C:3](=[O:12])[N:2]([CH3:1])[C:10]2[C:5]([C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

5

Reactant 3

HCID 702EthanolHCID 12192Ethyl diazoacetateHCID 16358N-Methylisatin

Product 1

HCID 86731081HCID 86731081, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Methylindoline-2,3-dione (5.0 g, 31.0 mmol) was stirred in DMF (15 mL) and Ethanol (85 mL) at 0° C. Ethyl 2-diazoacetate (4.51 mL, 43.4 mmol) was added. The ice bath was removed and the mixture was stirred at rt for two days. The mixture was evaporated to remove most of the EtOH. 1N HCl (ca. 100 mL) was added. It was stirred at rt for 3 h. LC-MS showed the desired ring expansion product. The precipitate was filtered and rinsed with H2O (2×) and dried under vacuum to give Intermediate 16 (5.05 g, 20.42 mmol, 94% yield) as slightly tan solids. LC-MS (ESI) 248.0 (M+H), RT=2.91 min (Method A).

Workup

  1. customat 0° C
  2. customThe ice bath was removed
  3. customThe mixture was evaporated
  4. customto remove most of the EtOH
  5. addition1N HCl (ca. 100 mL) was added
  6. stirringIt was stirred at rt for 3 h
  7. filtrationThe precipitate was filtered
  8. washrinsed with H2O (2×)
  9. customdried under vacuum

Sources & evidence

ORD record
ord-3c349b78dda7489d83b9c920df947c9e
Source dataset
uspto-grants-2015_02
Patent number
US08946430B2

Reaction notes

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