Stannous chloride dihydrate → HCID 57974946, compound

HRID 1865098Notes

Reaction equation

HRID 1865098 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:31])[C:8]([CH2:29][CH3:30])=[C:9]([C:27]#[N:28])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-])=O)=[CH:13][CH:12]=1)=[O:5])[CH3:2].O.O.[Sn](Cl)Cl>C(O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:31])[C:8]([CH2:29][CH3:30])=[C:9]([C:27]#[N:28])[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH2:24])=[CH:15][CH:16]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 69019545HCID 69019545, compound

Product 1

HCID 57974946HCID 57974946, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 4-cyano-5-ethyl-3-[4-(2-nitro-phenoxy)-phenyl]-1-methyl-1H-pyrole-2-carboxylic acid ethyl ester (prepared in example E-230) and tin(II) chloride dihydrate (5 Eq.) in absolute ethanol (20 mL), and heat at reflux with stirring under a nitrogen atmosphere for 3 hours. Cool the reaction mixture to room temperature and dilute with ethyl acetate. Wash the organic layer with water, dry over potassium carbonate, filter, and concentrate under reduced vacuum. Purify the material by silica gel chromatography eluting with methylene chloride to provide the title compound.

Workup

  1. temperatureat reflux
  2. washWash the organic layer with water
  3. dry with materialdry over potassium carbonate
  4. filtrationfilter
  5. concentrationconcentrate under reduced vacuum
  6. customPurify the material by silica gel chromatography
  7. washeluting with methylene chloride

Sources & evidence

ORD record
ord-29f8fbd8aac0419ea67e9b318872a53f
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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