Hydrochloric Acid → HCID 86695963, compound

HRID 2369576Notes

Reaction equation

HRID 2369576 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15]3[C:10](=[CH:11][N:12]=[C:13]([NH:16]C(=O)C)[CH:14]=3)[CH2:9][O:8][C:6]=2[CH:7]=1.Cl>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15]3[C:10](=[CH:11][N:12]=[C:13]([NH2:16])[CH:14]=3)[CH2:9][O:8][C:6]=2[CH:7]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86695933HCID 86695933, compound

Product 1

HCID 86695963HCID 86695963, compound

Procedure

N-(8-chloro-5H-chromeno[3,4-c]pyridin-2-yl)acetamide (0.05 g, 0.182 mmol) was taken up in 50% aqueous HCl (3 mL, 99 mmol) and refluxed for 3 h. The reaction mixture was cooled to room temperature and the volatiles were evaporated under reduced pressure. The residue was treated with water (3 mL) and extracted with dichloromethane (2×6 mL). The aqueous layer was collected and concentrated under reduced pressure to afford a 8-chloro-5H-chromeno[3,4-c]pyridin-2-amine, hydrochloride (50 mg, 0.185 mmol, quantitatively) as a yellow oil. LCMS (ESI) m/e 233.3 [(M+H)+, calcd for C12H10ClN2O 233.0]; LC/MS retention time (method G); tR=0.89 min

Workup

  1. temperaturerefluxed for 3 h
  2. customthe volatiles were evaporated under reduced pressure
  3. additionThe residue was treated with water (3 mL)
  4. extractionextracted with dichloromethane (2×6 mL)
  5. customThe aqueous layer was collected
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6eaca6afa74c4f4ca33fc79995a22157
Source dataset
uspto-grants-2014_04
Patent number
US08703953B2

Reaction notes

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