Hydrochloric Acid → HCID 178526802, compound

HRID 1525328Notes

Reaction equation

HRID 1525328 reaction equation
CN(C)[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5](OCC)=[O:6].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20](=[NH:22])[NH2:21])[N:15]=1.O(C)[Na].Cl>CO>[N+:10]([C:4]1[C:5]([OH:6])=[N:22][C:20]([C:16]2[N:15]=[N:14][CH:19]=[CH:18][CH:17]=2)=[N:21][CH:3]=1)([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 18756081Pyridazine-3-carboximidamideHCID 54330941ethyl 2-(N,N-dimethylaminomethylene)nitroacetate2×HCID 178418582HCID 178418582, compound

Product 1

HCID 178526802HCID 178526802, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 3-(dimethylamino)-2-nitroacrylate, 35i-f, (1 g, 5.3 mmol) and pyridazine-3-carboximidamide (0.8 g, 5.3 mmol) in CH3OH (30 mL) was added with NaOCH3 (3.4 g, 6.36 mmol) and refluxed overnight. The pH of reaction mixture was adjusted to 7 by addition of concentrated HCl. The solids were filtered to afford the product, 35i-g, (1 g, 86%). 1H NMR (300 MHz, DMSO) δ 7.77 (dd, J=4.8, 7.5 Hz, 2H), 8.29 (d, J=8.4 Hz, 1H), 8.77 (s, 1H), 9.26 (d, J=4.5 Hz, 1H). LC-MS (M+H)+ 220.1

Workup

  1. temperaturerefluxed overnight
  2. customThe pH of reaction mixture
  3. filtrationThe solids were filtered

Sources & evidence

ORD record
ord-c9241feb4cc344feb3e2f27ebf7bde16
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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