2-Aminopyridine → HCID 24770930, compound

HRID 1670688Notes

Reaction equation

HRID 1670688 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([N+:17]#[C-:18])=[CH:13][CH:12]=1)([O-:10])=[O:9].[CH:19]([C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[C:23]([O:25]C)=O)=O.Cl(O)(=O)(=O)=O.CC(C)([O-])C.[K+]>CO>[N+:8]([C:11]1[CH:12]=[CH:13][C:14]([N:17]2[C:18]3[N:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]4=[N:1][C:19]=3[C:21]3[C:22](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:23]2=[O:25])=[CH:15][CH:16]=1)([O-:10])=[O:9]

Participants

7

Reactant 5

HCID 104392-AminopyridineHCID 24247Perchloric AcidHCID 74802Benzene, 1-isocyano-4-nitro-HCID 243003Methyl 2-formylbenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 24770930HCID 24770930, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-aminopyridine (I1) (1.0 equiv., 5.30 mmol, 0.500 g), 4-nitrophenyl isocyanide (I2) (1.1 equiv., 5.80 mmol, 0.870 g), methyl 2-formylbenzoate (13) (1.1 equiv., 5.80 mmol, 0.960 g) and perchloric acid (0.1 equiv., 0.53 mmol, 0.053 g) in methanol (25 ml) was stirred at room temperature until no starting material was left. The progress of the reaction was monitored by LCMS. Potassium tert-butoxide (1.1 equiv., 5.80 mmol, 0.660 g) was added and the reaction mixture was further stirred at room temperature for 2 h. The resulting precipitate was filtered off and washed with isopropanol and isopropyl ether to give 6-(4-nitrophenyl)-pyrido[2′,1′:2,3]imidazo-[4,5-c]isoquinolin-5(6H)-one (1) (1.20 g, yield=63%, purity (LC)=95%).

Workup

  1. waitwas left
  2. stirringthe reaction mixture was further stirred at room temperature for 2 h
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with isopropanol and isopropyl ether

Sources & evidence

ORD record
ord-101adf194cae4e6b80b397a6465dab86
Source dataset
uspto-grants-2011_08
Patent number
US07994187B2

Reaction notes

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