Ammonium Chloride → HCID 68283386, compound

HRID 624047Notes

Reaction equation

HRID 624047 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][N:14]1[CH:18]=[C:17]([N+:19]([O-])=O)[N:16]=[CH:15]1.[NH4+:22].[Cl-]>CCO.O.[Fe]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][N:14]1[CH:18]=[C:17]([NH2:19])[N:16]=[CH:15]1.[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][N:14]1[C:18]([NH2:22])=[CH:17][N:16]=[CH:15]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86704215HCID 86704215, compound

Product 2

HCID 68283386HCID 68283386, compoundHCID 86704214HCID 86704214, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 5-methoxy-3-(2-(4-nitro-1H-imidazol-1-yl)ethyl)-1H-indole in EtOH/H2O (1.8 mL/0.9 mL), NH4Cl (158 mg, 2.95 mmol) and Fe (99 mg, 1.77 mmol) was added. The resulting black mixture was heated to 85° C. for 30 min, then it was filtered while hot and the filter cake was rinsed with EtOH. The filtrate was concentrated in vacuo and the residue partitioned between DCM and aq. 1 N NaOH-solution. The org. layer was separated and the aq. layer wa extracted with DCM. The combined organic extracts were washed with brine, dried (MgSO4), filtered and the solvents were removed under reduced pressure to yield the title compound in mixture with 1-(2-(5-methoxy-1H-indol-3-yl)ethyl)-1H-imidazol-5-amine as a dark brown solid, which was used in the next step without further purification. LC-MS conditions A: tR=0.52 min, [M+H]+=257.22.

Workup

  1. filtrationit was filtered while hot and the filter cake
  2. washwas rinsed with EtOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue partitioned between DCM and aq. 1 N NaOH-solution
  5. customlayer was separated
  6. extractionthe aq. layer wa extracted with DCM
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-3220747d4d92475aaec17a66c468a430
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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