Hydrochloric Acid → HCID 25222140, compound

HRID 2096994Notes

Reaction equation

HRID 2096994 reaction equation
Cl.[NH4+].[Cl-].[CH2:4]([NH:11][C:12]1[CH:17]=[C:16]([N+:18]([O-])=O)[N:15]=[C:14]2[N:21]([CH:24]([CH3:26])[CH3:25])[CH:22]=[N:23][C:13]=12)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CCO.[Fe]>[NH2:18][C:16]1[N:15]=[C:14]2[N:21]([CH:24]([CH3:25])[CH3:26])[CH:22]=[N:23][C:13]2=[C:12]([NH:11][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 25222139HCID 25222139, compound

Product 1

HCID 25222140HCID 25222140, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a suspension of 5.5 g of Fe in 30 mL EtOH was added slowly 2 mL 12 N HCl. The mixture was stirred at 75° C. for 1 hour. After cooling at 65° C., 12 mL 25% NH4Cl solution was added. The mixture was stirred 5 min and 6a (0.02 mol, in 5 mL EtOH) was added. The mixture is heated at 75° C. for 2 hour. After cooling to rt, 5 g celite was added the mixture was filtrated on celite and the remaining solids were washed several times with ethanol. The combined filtrates were concentrated and extracted with a CH2Cl2 and 10% Na2CO3. Concentration of the organic layer led to crystallisation of the amine IIb. Yield 98%.

Workup

  1. temperatureAfter cooling at 65° C.
  2. stirringThe mixture was stirred 5 min
  3. temperatureThe mixture is heated at 75° C. for 2 hour
  4. temperatureAfter cooling to rt
  5. addition5 g celite was added the mixture
  6. filtrationwas filtrated on celite
  7. washthe remaining solids were washed several times with ethanol
  8. concentrationThe combined filtrates were concentrated
  9. extractionextracted with a CH2Cl2 and 10% Na2CO3
  10. customConcentration of the organic layer led to crystallisation of the amine IIb

Sources & evidence

ORD record
ord-c2bde66467d84d3aafaba31b86006278
Source dataset
uspto-grants-2013_05
Patent number
US08450342B2

Reaction notes

Loading…