4-Carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride → HCID 10540454, compound

HRID 964011Notes

Reaction equation

HRID 964011 reaction equation
[O:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([NH2:10])[C:2]1=2.[Cl-:11].[C:12]([C:15]1[CH:20]=[CH:19][N+](C2C=CC([N+]([O-])=O)=CC=2[N+]([O-])=O)=[CH:17][CH:16]=1)(=[O:14])[NH2:13]>CO>[Cl-:11].[O:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([N+:10]3[CH:19]=[CH:20][C:15]([C:12](=[O:14])[NH2:13])=[CH:16][CH:17]=3)[C:2]1=2

Participants

4

Reactant 2

HCID 106160034-Carbamoyl-1-(2,4-dinitrophenyl)pyridinium chlorideHCID 128059502,3-Dihydro-1-benzofuran-7-amine

Product 1

HCID 10540454HCID 10540454, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2,3-dihydrobenzo[b]furan-7-ylamine (6.8 g prepared in a similar manner to that described in Tetrahedron Letters 1982,23,147), 4-carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride (14.7 g prepared in a similar manner to that described in Example 2) and methanol (400 ml) was stirred under reflux for 5 hours then allowed to stand at ambient temperature and heated for 16 hours. The solvent was removed in vacuo, and the residue was triturated with hot acetone, cooled and filtered to give 1-(2,3-dihydrobenzo[b]furan-7-yl)-4-carbamoylpyridinium chloride as a yellow solid (11.5 g), m.p. 289°-290° C.

Workup

  1. customprepared in a similar manner to that
  2. customprepared in a similar manner to that
  3. temperatureunder reflux for 5 hours
  4. customto stand at ambient temperature
  5. temperatureheated for 16 hours
  6. customThe solvent was removed in vacuo
  7. customthe residue was triturated with hot acetone
  8. temperaturecooled
  9. filtrationfiltered

Sources & evidence

ORD record
ord-0fc4e65ccaaa485c857668d0d2669af8
Source dataset
uspto-grants-1998_06
Patent number
US05767116

Reaction notes

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