Ammonium Chloride → HCID 65343320, compound

HRID 1051459Notes

Reaction equation

HRID 1051459 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:7]=1.[NH4+].[Cl-]>CCO.O.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([NH:8][CH:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[C:5]([NH2:15])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 65341357HCID 65341357, compound

Product 1

HCID 65343320HCID 65343320, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-(5-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-amine (2.5 g, 8.333 mmol) in EtOH/H2O (1:1) (50 mL) was added iron powder (2.8 g, 50 mmol) and NH4Cl (2.65 g, 50 mmol). The reaction mixture was heated at 60° C. for 12 h. After filtering the reaction mixture, the resulting filtrate was extracted with DCM with the separated organic layer dried over sodium sulfate, filtered and concentrated to obtain crude product which was used in next step without further purification.

Workup

  1. filtrationAfter filtering the reaction mixture
  2. extractionthe resulting filtrate was extracted with DCM with the separated organic layer
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto obtain crude product which
  7. customwas used in next step without further purification

Sources & evidence

ORD record
ord-1ee859f3f5ef47619fc6765bdafb20f8
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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