Hydrochloric Acid → HCID 67455856, compound

HRID 639697Notes

Reaction equation

HRID 639697 reaction equation
[CH2:1]([N:4]([CH2:24][CH:25]=[CH2:26])[C:5]1[C:10]([N+:11]([O-])=O)=[C:9]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]([CH3:22])=[C:7]([CH3:23])[N:6]=1)[CH:2]=[CH2:3].Cl.O.[OH-].[Na+]>C(O)C.[Fe]>[CH2:24]([N:4]([CH2:1][CH:2]=[CH2:3])[C:5]1[C:10]([NH2:11])=[C:9]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]([CH3:22])=[C:7]([CH3:23])[N:6]=1)[CH:25]=[CH2:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67457450HCID 67457450, compound

Product 1

HCID 67455856HCID 67455856, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

N2,N2-Diallyl-N4-benzyl-5,6-dimethyl-3-nitro-pyridine-2,4-diamine (828 mg, 2.4 mmol) was dissolved in ethanol (15 mL) and 2N HCl (15 mL) and iron powder (527 mg, 9.6 mmol) was added in one portion. The reaction mixture was heated at 70° C. for 2 h, and then cooled to room temperature and poured into 50 mL water. The resulting solution was neutralised with 1N NaOH solution to give a dark green suspension, which was extracted with EtOAc (2×25 mL) and the combined organics were dried over MgSO4, filtered and evaporated to give the title compound as a dark green oil (559 mg, 74%).

Workup

  1. temperaturecooled to room temperature
  2. customto give a dark green suspension, which
  3. extractionwas extracted with EtOAc (2×25 mL)
  4. dry with materialthe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-7cc5976b6fe946e1a5116fd58f6b6a3b
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

Loading…