Ethanol → ethyl 1-acetyl-2,3-dihydro-5-methoxy-1H-indole-2-carboximidate monohydrochloride

HRID 1246205Notes

Reaction equation

HRID 1246205 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:15]#[N:16])(=[O:3])[CH3:2].[CH2:17]([OH:19])[CH3:18].[ClH:20].C(OCC)C>>[ClH:20].[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:15](=[NH:16])[O:19][CH2:17][CH3:18])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 10953452Ether hydrochlorideHCID 219141141-acetyl-2,3-dihydro-5-methoxy-1H-indole-2-carbonitrile

Product 1

HCID 21914094ethyl 1-acetyl-2,3-dihydro-5-methoxy-1H-indole-2-carboximidate monohydrochloride

Procedure

To a solution of intermediate (23) (0.0154 mole) and ethanol (0.0231 mole) in 1M HCl/diethylether (200 ml), cooled in an ice bath was bubbled HCl (gas) for 60 minutes. The ice bath was maintained for 45 minutes, and the mixture was concentrated at room temperature under vacuum to 200 ml of an oily precipitate. The residue was triturated to a brown solid that became an oil after decanting off the diethylether. The residue was washed with diethylether twice, dissolved in methanol, and used without further purification for further synthesis, yielding ethyl 1-acetyl-2,3-dihydro-5-methoxy-1H-indole-2-carboximidate monohydrochloride (intermediate 24).

Workup

  1. customwas bubbled HCl (gas) for 60 minutes
  2. temperatureThe ice bath was maintained for 45 minutes
  3. concentrationthe mixture was concentrated at room temperature under vacuum to 200 ml of an oily precipitate
  4. customThe residue was triturated to a brown solid that
  5. customafter decanting off the diethylether
  6. washThe residue was washed with diethylether twice
  7. dissolutiondissolved in methanol
  8. customused without further purification for further synthesis

Sources & evidence

ORD record
ord-11589e480d7845b8aa46b7fa631597ea
Source dataset
uspto-grants-2006_10
Patent number
US07125891B2

Reaction notes

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