Hydrochloric Acid → HCID 86670220, compound

HRID 2091607Notes

Reaction equation

HRID 2091607 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[C:8](=[O:12])[N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]2.Cl>C(Cl)Cl.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86670219HCID 86670219, compound

Product 1

HCID 86670220HCID 86670220, compoundYield 191.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 6-chloro-1-oxo-3,4-dihydro-2,7-naphthyridine-2(1H)-carboxylate (3.0 g, 10.6 mmol) in DCM (20 mL) was added 4N HCl solution in dioxane (10 mL). After stirring 20 minutes at room temperature, the reaction was diluted with DCM (50 mL, then sonicated and filtered to give 6-chloro-3,4-dihydro-2,7-naphthyridin-1(2H)-one hydrochloride (2.22 g, 93% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.70 (s, 1H), 8.23 (br. s., 1H), 7.57 (s, J=0.6 Hz, 1H), 3.40 (t, J=6.6, 2.8 Hz, 2H), 2.96 (t, J=6.6 Hz, 2H); MS (EI) m/z=183.6 [M+1]+.

Workup

  1. customsonicated
  2. filtrationfiltered

Sources & evidence

ORD record
ord-3f251312526b4a7fb9e69fa29b72db38
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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