Ammonium Chloride → HCID 67418988, compound

HRID 1799047Notes

Reaction equation

HRID 1799047 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-])=O)=[C:6]([NH:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=2)[CH:7]=1.[Cl-].[NH4+]>C(O)C.[Fe]>[NH2:17][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=1[NH:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N:10]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67442189HCID 67442189, compound

Product 1

HCID 67418988HCID 67418988, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a well stirred solution of step 1 intermediate (2.5 g, 9.1 mmol) in ethanol (45 ml), aqueous solution of ammonium chloride (4.87 g, 91.0 mmol) was added and the reaction mixture was refluxed at 100° C. After 15 minutes iron powder (1.5 g, 27 mmol) was added to it portionwise and was further refluxed for 2 h. After the completion of reaction, excess of ethanol was evaporated under reduced pressure; the reaction mixture was diluted with chloroform (200 ml) and filtered through celite bed. The combined organic layers were washed with water (2×50 ml) and brine, dried (Na2SO4), filtered and concentrated under reduced pressure to yield 1.8 g of the product.

Workup

  1. temperaturewas further refluxed for 2 h
  2. customAfter the completion of reaction
  3. customexcess of ethanol was evaporated under reduced pressure
  4. additionthe reaction mixture was diluted with chloroform (200 ml)
  5. filtrationfiltered through celite bed
  6. washThe combined organic layers were washed with water (2×50 ml) and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd45e07b15214efaabfa74936eb5e1c8
Source dataset
uspto-grants-2013_01
Patent number
US08344010B2

Reaction notes

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