Ammonium Chloride → HCID 59540224, compound

HRID 923403Notes

Reaction equation

HRID 923403 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][N:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O1CCCC1.O.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[C:10](=[O:12])[CH3:11])=[CH:23][CH:24]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 59540465HCID 59540465, compound

Product 1

HCID 59540224HCID 59540224, compoundYield 110.6%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product from Example 68A (250 mg, 0.759 mmol), iron powder (424 mg, 7.59 mmol), and ammonium chloride (203 mg, 3.80 mmol) in ethanol (1 mL), tetrahydrofuran (1 mL) and water (0.250 mL) was heated at 80° C. for 18 hours. The mixture was allowed to cool to rt, filtered, rinsed with methanol, and concentrated in vacuo. The residue was partitioned between EtOAc and H2O, and the organic layer was dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound (226 mg, 90%). MS (ESI) m/z 269.9 (M+H)+

Workup

  1. temperatureto cool to rt
  2. filtrationfiltered
  3. washrinsed with methanol
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between EtOAc and H2O
  6. dry with materialthe organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f014b42469b49a9b41300b4c5be5990
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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