Hydrochloric Acid → HCID 24771030, compound

HRID 1670706Notes

Reaction equation

HRID 1670706 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](OC)=O)=[O:20].Cl(O)(=O)(=O)=[O:32].CC(C)([O-])C.[K+].Cl>CO.C(O)(=O)C>[OH:32][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:4]=1)[C:18]1[N:17]([C:14]3[CH:13]=[CH:12][C:11]([N+:8]([O-:10])=[O:9])=[CH:16][CH:15]=3)[C:19](=[O:20])[C:21]3[C:22]([C:23]=1[N:1]=2)=[CH:27][CH:28]=[CH:29][CH:30]=3

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 104392-AminopyridineHCID 24247Perchloric AcidHCID 74802Benzene, 1-isocyano-4-nitro-HCID 243003Methyl 2-formylbenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 24771030HCID 24771030, compoundYield 338.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 2-aminopyridine (I1) (1.0 equiv., 27.2 mmol, 3.00 g), 4-nitrophenyl isocyanide (1.1 equiv., 29.9 mmol, 4.40 g), methyl 2-formylbenzoate (1.1 equiv., 29.9 mmol, 4.9 g) and perchloric acid (0.2 equiv., 5.4 mmol, 0.55 g) in methanol was stirred at room temperature overnight. Potassium tert-butoxide (2.2 equiv., 59.8 mmol, 6.7 g) was added and the reaction mixture was further stirred at room temperature for 2 h. Acetic acid (2.0 ml) (or concentrated hydrochloric acid) was added, the resulting precipitate was filtered off and washed with isopropanol and isopropyl ether to give 9-hydroxy-6-(4-nitrophenyl)-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one (10) (6.80 g, yield=67%, purity (LC)=95%).

Workup

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

Sources & evidence

ORD record
ord-21bff4fcf27a41f9ae2b834738c5e2e1
Source dataset
uspto-grants-2011_08
Patent number
US07994187B2

Reaction notes

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