Hydrochloric Acid → 6-Chloro-1H-pyrrolo[3,2-c]pyridine

HRID 1619122Notes

Reaction equation

HRID 1619122 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5](/[CH:9]=[CH:10]/OCC)=[CH:4][N:3]=1.Cl>CO>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:9]=[CH:10][NH:8][C:6]=2[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 577993422-Chloro-5-[(1E)-2-ethoxyethenyl]-4-pyridinamine

Product 1

HCID 125755166-Chloro-1H-pyrrolo[3,2-c]pyridineYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 2-chloro-5-[(E)-2-ethoxyvinyl]pyridin-4-amine (preparation 36b, 1.00 g, 5.30 mmol) in methanol (20 mL) was added concentrated hydrochloric acid (1.00 mL, 32.64 mmol) and the mixture was stirred at 75° C. for 21 h. The mixture was concentrated under reduced pressure, treated with a saturated aqueous solution of potassium carbonate and extracted with ethyl acetate. The organic layer was dried and evaporated to yield the title compound (0.76 g, 99%) as a beige solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiontreated with a saturated aqueous solution of potassium carbonate
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-05bbf51b24c74629bfdaab249db2ca2f
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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