Hydrochloric Acid → HCID 86704558, compound

HRID 1022428Notes

Reaction equation

HRID 1022428 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH3:11])[C:6]=2[CH:5]=[C:4]([Cl:12])[N:3]=1.[OH-:13].[Na+].Cl>O1CCOCC1>[Cl:12][C:4]1[NH:3][C:2](=[O:13])[C:7]2[CH:8]=[CH:9][N:10]([CH3:11])[C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 140553384,6-Dichloro-1-methyl-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 86704558HCID 86704558, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
160 °C

Procedure

A microwave reaction vial was charged with 4,6-dichloro-1-methyl-1H-pyrrolo[3,2-c]pyridine (60 mg, 0.29 mmol), a 2M aqueous sodium hydroxide solution (10 mL) and 1,4-dioxane (1 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-methyl-1,5-dihydro-pyrrolo[3,2-c]pyridine-4-one (51 mg, 93.6%). LC-MS calcd. for C8H7ClN2O2 [(M+H)+] 183, obsd. 182.9.

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-6fff99f580fa41e3afd804b19a0f18c9
Source dataset
uspto-grants-2014_05
Patent number
US08722661B2

Reaction notes

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