Ethanol → HCID 21914116, compound

HRID 887921Notes

Reaction equation

HRID 887921 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:14]#[N:15])(=[O:3])[CH3:2].[CH2:16]([OH:18])[CH3:17].[ClH:19].C(OCC)C>>[ClH:19].[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:14](=[NH:15])[O:18][CH2:16][CH3:17])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 10953452Ether hydrochlorideHCID 21914140HCID 21914140, compound

Product 1

HCID 21914116HCID 21914116, compound

Procedure

A solution of intermediate (19) (0.004 mole) and HCl/diethylether (60 mL) was cooled in an ice bath under argon. Ethanol (0.0075 mole) was added. HCl was bubbled into the solution for 50 minutes until the mixture became homogeneous. The mixture was allowed to slowly warm to room temperature and stir for 4 hours. The ether was decanted off and dissolved in methanol. The methanol solution was concentrated in vacuum and the residue was used as is for the next step, yielding ethyl 1-acetyl-5-fluoro-2,3-dihydro-1H-indole-2-carboximidate monohydrochloride (intermediate 20).

Workup

  1. customHCl was bubbled into the solution for 50 minutes until the mixture
  2. customThe ether was decanted off
  3. dissolutiondissolved in methanol
  4. concentrationThe methanol solution was concentrated in vacuum

Sources & evidence

ORD record
ord-1d637c649b57483884b5beb1f673f949
Source dataset
uspto-grants-2012_08
Patent number
US08247432B2

Reaction notes

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