Hydrochloric Acid → 1-phenyl-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium chloride

HRID 2383431Notes

Reaction equation

HRID 2383431 reaction equation
[C:1]1([C:7]2[C:19]3[C:18]4[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C:13]=4[CH:12]=[N:11][C:10]=3[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:27].O1CCOCC1>ClCCl>[Cl-:27].[C:1]1([C:7]2[C:19]3[C:18]4[CH2:17][CH2:16][NH2+:15][CH2:14][C:13]=4[CH:12]=[N:11][C:10]=3[NH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178451612tert-butyl 1-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate

Product 1

HCID 1784779931-phenyl-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium chlorideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 1-phenyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate (0.21 g, 0.60 mmol) in dichloromethane (5 mL) was added 4 M solution of HCl gas in 1,4-dioxane (1.5 mL, 6.0 mmol). The reaction was shaken at room temperature for 16 hours. A yellow solid precipitated out in the reaction mixture, which was filtered to give the pure desired product, 1-phenyl-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium chloride (0.184 g, 95%) as a yellow solid; M.p.=265° C. decomposition; 400 MHz 1H NMR (DMSO-d6) δ: 13.91 (s, 1H), 9.39 (s, 2H), 8.43 (s, 1H), 7.62-7.46 (m, 5H), 4.44-3.38 (m, 2H), 3.38-3.2 (m, 2H), 3.01 (t, J=6.4 Hz, 2H); LCMS [M+H]: 251.

Workup

  1. customA yellow solid precipitated out in the reaction mixture, which
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-2ebf26143ec6451b84c47257d3ce30c0
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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