Hydrochloric Acid → HCID 67337516, compound

HRID 1678324Notes

Reaction equation

HRID 1678324 reaction equation
[Cl-:1].[NH3+:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[NH+:11][CH:12]=[CH:13][CH:14]=1)=O.[Cl-].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:29][C:26]([CH:27]=O)=[CH:25][CH:24]=2)=[C:19]([N+:30]([O-:32])=[O:31])[CH:18]=1.Cl>C(O)(C)C>[ClH:16].[ClH:1].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:29][C:26]([CH:27]=[C:6]3[CH2:5][CH2:4][CH2:3][N:2]=[C:7]3[C:9]3[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=3)=[CH:25][CH:24]=2)=[C:19]([N+:30]([O-:32])=[O:31])[CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12682865-(4-Chloro-2-nitrophenyl)furan-2-carbaldehydeHCID 673376573-(5-Ammoniopentanoyl)pyridinium chloride

Product 1

HCID 67337516HCID 67337516, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

3-(5-Ammoniopentanoyl)pyridinium chloride (109 mg, 0.43 mmol) and 5-(4-chloro-2-nitrophenyl)furfural (131 mg, 0.52 mmol) were combined in a reaction vessel and treated with isopropanol (6 mL). The reaction vessel was sealed and the reaction was heated to 80° C. with stirring overnight. The reaction was then cooled to room temperature, concentrated under reduced pressure and treated with saturated NaHCO3(aq). This mixture was then extracted three times with EtOAc. The EtOAc extracts were washed with brine, combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The recovered material was eluted through a 20 gram column of silica gel with 10.5:7:7:1:0.1 hexane:MtBE:CH2Cl2:MeOH:NH4OH (800 mL). One sample was recovered. This material was dissolved into methanol and treated with 2 equivalents of 6 N HCl(aq). This solution was concentrated under reduced pressure and the recovered material re-crystallized from a mix of isopropanol and ether. The crystals were recovered by vacuum filtration, washed with a 20% solution of isopropanol in hexane, and then with ether, then dried under vacuum giving 95 mg (47%) of a yellow solid. LC-MS: RT=5.65 min, [M+H]+=394.0.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction was then cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additiontreated with saturated NaHCO3(aq)
  5. extractionThis mixture was then extracted three times with EtOAc
  6. washThe EtOAc extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. washThe recovered material was eluted through a 20 gram column of silica gel with 10.5:7:7:1:0.1 hexane
  11. customOne sample was recovered
  12. dissolutionThis material was dissolved into methanol
  13. concentrationThis solution was concentrated under reduced pressure
  14. customthe recovered material re-crystallized from
  15. additiona mix of isopropanol and ether
  16. filtrationThe crystals were recovered by vacuum filtration
  17. washwashed with a 20% solution of isopropanol in hexane
  18. dry with materialwith ether, then dried under vacuum

Sources & evidence

ORD record
ord-3b143e1e388c4625b5cb1bfa9754dd7c
Source dataset
uspto-grants-2011_08
Patent number
US08008499B2

Reaction notes

Loading…