Ammonium Chloride → HCID 59540375, compound

HRID 923442Notes

Reaction equation

HRID 923442 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([N+:22]([O-])=O)[CH:16]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[N+:27]([O-])=O.[Cl-].[NH4+]>CCO.C1COCC1.O.[Fe]>[NH2:27][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:2]=1[Cl:1])[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([NH2:22])[CH:16]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 59540220HCID 59540220, compound

Product 1

HCID 59540375HCID 59540375, compoundYield 99%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of product from Example 148C (0.304 g, 0.703 mmol) in EtOH (10 mL), THF (10 mL) and H2O (2.5 mL) was added iron powder (0.393 g, 7.03 mmol), followed by addition of ammonium chloride (0.188 g, 3.52 mmol). The resulting mixture was stirred at 90° C. for 2 hrs and then filtered through celite and washed with ethanol. The filtrate was concentrated in vacuo, and the residue was partitioned between CH2Cl2 and H2O, and the organic layer was dried over anhydrous Na2SO4. The drying agent was filtered off, and solvent was removed in vacuo to give a crude product that was purified by column chromatography on silica gel using a solvent gradient 0-0.1% MeOH in CH2Cl2 to afford the title compound (0.259 gm, 99%).

Workup

  1. filtrationfiltered through celite
  2. washwashed with ethanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was partitioned between CH2Cl2 and H2O
  5. dry with materialthe organic layer was dried over anhydrous Na2SO4
  6. filtrationThe drying agent was filtered off
  7. customsolvent was removed in vacuo
  8. customto give a crude product that
  9. customwas purified by column chromatography on silica gel using a solvent gradient 0-0.1% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-004293a050e346f295b5896217fdc00a
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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