Hydrochloric Acid → HCID 178511859, compound

HRID 732108

Reaction equation

HRID 732108 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([Cl:10])[N:3]=1.C[O-].[Na+].Cl.[CH:15]1([NH2:18])[CH2:17][CH2:16]1>CCO.CO>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Cl:10])[N:3]=1)[C:8]([NH:18][CH:15]1[CH2:17][CH2:16]1)=[NH:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 69828CyclopropylamineHCID 7359062,6-DichloroisonicotinonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 178511859HCID 178511859, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

2,6-dichloropyridine-4-carbonitrile (5 g, 28.9 mmol), methanol (50 ml) and sodium methoxide (0.66 ml, 2.89 mmol) were mixed and stirred at r.t. for 3 h. HCl in EtOH (24% w/w, 10 ml) and cyclopropylamine (3 mL, 43.4 mmol) were added at 0° C., followed by stirring at r.t. o.n. The reaction mixture was concentrated in-vacuo. The isolated residue was treated with cold aq. NaOH (1N, 75 ml) and extracted with EA. The combined organic phase was washed sequentially with aq. NaOH and brine, dried (Na2SO4), filtered and concentrated in-vacuo. The isolated residue was triturated with Et2O to isolate the title compound (3.82 g). 1H-NMR: 7.59 (br. s, 2H), 4.96 (br. s, 2H), 2.60 (m, 1H), 0.90 (m, 2H), 0.69 (m, 2H).

Workup

  1. stirringby stirring at r.t. o.n
  2. concentrationThe reaction mixture was concentrated in-vacuo
  3. additionThe isolated residue was treated with cold aq. NaOH (1N, 75 ml)
  4. extractionextracted with EA
  5. washThe combined organic phase was washed sequentially with aq. NaOH and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in-vacuo
  9. customThe isolated residue was triturated with Et2O

Sources & evidence

ORD record
ord-e2e554707a4e41a989ac5db57b31e505
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Linked notes

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