Ammonium Chloride → HCID 59540227, compound

HRID 923437Notes

Reaction equation

HRID 923437 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([N:6]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=2)[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)=[CH:4][CH:3]=1.[Cl-].[NH4+]>C1COCC1.C(O)C.O.[Fe]>[NH2:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH2:7][N:6]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=1)[C:5]1[CH:27]=[CH:28][C:2]([F:1])=[CH:3][CH:4]=1

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 59540289HCID 59540289, compound

Product 1

HCID 59540227HCID 59540227, compoundYield 85%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a slurry of the product from Example 143A (0.450 g, 1.180 mmol) in THF (4 mL), ethanol (1.00 mL) and water (4.00 mL) at rt was added ammonium chloride (0.189 g, 3.54 mmol) followed by iron (0.329 g, 5.90 mmol) and the mixture heated to 80° C. After 3 h, the mixture was filtered through Celite, concentrated and the residue partitioned between water and 25% isopropyl alcohol-CHCl3. The organic phase was dried (Na2SO4) and concentrated. The solid was dried in a vacuum oven to provide 321 mg (85%) of the title compound. MS (ESI; M+H) m/z=322.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationconcentrated
  3. customthe residue partitioned between water and 25% isopropyl alcohol-CHCl3
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-2318f67e82424ab3b831bd4ee1707720
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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