Hydrochloric Acid → HCID 86704560, compound

HRID 1022430Notes

Reaction equation

HRID 1022430 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH2:11][CH3:12])[C:6]=2[CH:5]=[C:4]([Cl:13])[N:3]=1.[OH-:14].[Na+].Cl>O1CCOCC1>[Cl:13][C:4]1[NH:3][C:2](=[O:14])[C:7]2[CH:8]=[CH:9][N:10]([CH2:11][CH3:12])[C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86704559HCID 86704559, compound

Product 1

HCID 86704560HCID 86704560, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

A microwave reaction vial was charged with 4,6-dichloro-1-ethyl-1H-pyrrolo[3,2-c]pyridine (200 mg, 0.930 mmol), a 2M aqueous sodium hydroxide solution (10 mL) and 1,4-dioxane (3 mL). The vial was sealed and then heated in the microwave at 160° C. for 30 min. At this time, the resulting mixture was acidified to pH 6.5 with a 4M aqueous hydrochloric acid solution and then concentrated in vacuo. The residue was diluted with ethanol. The solids were removed by filtration, and the filtrate was concentrated in vacuo. Flash chromatography (10/1 methylene chloride/methanol) afforded 6-chloro-1-ethyl-1,5-dihydro-pyrrolo[3,2-c]pyridine-4-one (60 mg, 32.8%). LC-MS calcd. for C9H9ClN2O [(M)+] 196, obsd. 196.9.

Workup

  1. customA microwave reaction
  2. customThe vial was sealed
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with ethanol
  5. customThe solids were removed by filtration
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7f3b7028ac86409e9095ea7037dc20bd
Source dataset
uspto-grants-2014_05
Patent number
US08722661B2

Reaction notes

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