Hydrochloric Acid → HCID 59595966, compound

HRID 2264181Notes

Reaction equation

HRID 2264181 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[C:9]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[N:10][C:11]([NH2:17])=[C:12]([N+:14]([O-])=O)[CH:13]=1.Cl>CCO.[Fe]>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[C:9]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[N:10][C:11]([NH2:17])=[C:12]([NH2:14])[CH:13]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59595961HCID 59595961, compound

Product 1

HCID 59595966HCID 59595966, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

3″-chloro-5′-nitro-3,2′:3′,4″-terpyridin-6′-amine (127 mg, 0.39 mmol) was dissolved in EtOH (4.0 mL) and conc. HCl (245 μL). Iron metal (109 mg, 1.09 mmol) was added to the suspension and the mixture was heated to 70° C. for 1 h. The suspension was then filtered through Celite® and the solvent removed in vacuo. NaHCO3 (20 mL of a 4% w/w aqueous solution) was added to the residue and the aqueous phase was extracted with AcOEt (3×20 mL). The organic layer was dried, filtered and concentrated to dryness to yield the title compound (52 mg, 45%), which was used without further purification.

Workup

  1. filtrationThe suspension was then filtered through Celite®
  2. customthe solvent removed in vacuo
  3. additionNaHCO3 (20 mL of a 4% w/w aqueous solution) was added to the residue
  4. extractionthe aqueous phase was extracted with AcOEt (3×20 mL)
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-09383e8c7cf74b33bb3808436d661162
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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