Ammonium Chloride → HCID 57625538, compound

HRID 2387477Notes

Reaction equation

HRID 2387477 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([CH3:24])[CH:16]=2)[C:11](=[O:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([N:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][C:11]2=[O:25])=[CH:16][C:17]=1[CH3:24]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 57625512HCID 57625512, compound

Product 1

HCID 57625538HCID 57625538, compoundYield 94.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-(benzyloxy)-1-(3-methyl-4-nitrophenyl)pyridin-2(1H)-one (0.940 mg, 2.79 mmol) in EtOH (19.2 mL) and H2O (4.8 mL) was treated with iron powder (1.35 g, 24.2 mmol) and NH4Cl (64.1 mg). After stirring at reflux for two hours, the reaction mixture was filtered through Celite and the filtrate concentrated to yield the title compound (0.804 g, 94%) as an off-white solid 1H NMR (500 MHz, DMSO-d6) δ 7.45-7.34 (m, 6H), 6.85 (s, 1H), 6.81 (d, J=8.5 Hz, 1H), 6.62 (d, J=8.0 Hz, 1H), 6.00 (dd, J=7.5, 5.0 Hz, 1H), 5.90 (d, J=2.0 Hz, 1H), 5.11 (s, 2H), 5.03 (s, 2H), 2.60 (s, 3H).

Workup

  1. temperatureat reflux for two hours
  2. filtrationthe reaction mixture was filtered through Celite
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-0e262bd2e35b4bb1a50ea3dd9d245287
Source dataset
uspto-grants-2012_09
Patent number
US08268868B2

Reaction notes

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