Ammonium Chloride → HCID 57625530, compound

HRID 2390439Notes

Reaction equation

HRID 2390439 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[CH:13][C:12]2=[O:27])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.[NH4+].[Cl-]>[Fe].CCO.O>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([N:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=3)=[CH:13][C:12]2=[O:27])=[CH:3][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 57625526HCID 57625526, compound

Product 1

HCID 57625530HCID 57625530, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A solution of 1-(3-methyl-4-nitrophenyl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one (0.46 g, 1.2 mmol) in 9:1 EtOH/H2O (20 mL) was treated with iron powder (0.62 g, 11.1 mmol) and NH4Cl (33 mg, 0.61 mmol), and the resulting suspension was heated at reflux for 18 h. The reaction mixture was filtered, while hot, through Celite® with portions of CH2Cl2 (2×25 mL) and MeOH (2×25 mL). The filtrates were combined and made basic with 1 N NaOH (10 mL). The solution was extracted with CH2Cl2 (2×40 mL) and the combined organic extracts were dried over Na2SO4, filtered and concentrated to provide the title compound (0.409 g, 100%) as a yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 7.97 (d, J=8.0 Hz, 2H), 7.85 (d, J=8.5 Hz, 2H), 7.68 (d, J=7.0 Hz, 1H), 6.96 (s, 1H), 6.92 (dd, J=8.5, 2.0 Hz, 1H), 6.80 (d, J=1.5 Hz, 1H), 6.67 (d, J=8.0 Hz, 1H), 6.63 (dd, J=7.0, 2.0 Hz, 1H), 5.11 (s, 2H), 2.09 (s, 3H).

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureat reflux for 18 h
  3. filtrationThe reaction mixture was filtered
  4. extractionThe solution was extracted with CH2Cl2 (2×40 mL)
  5. dry with materialthe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8e6ab454db1c439689a71d01412e1c72
Source dataset
uspto-grants-2012_09
Patent number
US08273770B2

Reaction notes

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