Ammonium Chloride → 5-Amino-3-chloro-1-methyl-1,2-dihydropyridin-2-one

HRID 873800Notes

Reaction equation

HRID 873800 reaction equation
[Cl:1][C:2]1[C:3](=[O:12])[N:4]([CH3:11])[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1.[NH4+].[Cl-]>[Fe].CCO>[NH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3](=[O:12])[N:4]([CH3:11])[CH:5]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 867031063-chloro-1-methyl-5-nitropyridin-2(1H)-one

Product 1

HCID 717560735-Amino-3-chloro-1-methyl-1,2-dihydropyridin-2-oneYield 78%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 3-chloro-1-methyl-5-nitropyridin-2(1H)-one (Step 5.1) (10.38 g, 55.0 mmol), EtOH (200 mL) and NH4Cl (79 mL, 550 mmol) was added iron (9.22 g, 165 mmol). The reaction mixture was stirred for 1 hr at 85° C., filtered through a pad of celite, and concentrated. The crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 2-10%) to afford the title product (6.77 g, 42.7 mmol, 78% yield) as a black solid. tR: 0.29 min (LC-MS 1); ESI-MS: 159 [M+H]+ (LC-MS 1); Rf=0.28 (CH2Cl2/MeOH 9:1).

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationconcentrated
  3. customThe crude material was purified by silica gel column chromatography (CH2Cl2/MeOH 2-10%)

Sources & evidence

ORD record
ord-285d7c991a7541febff07280f478416e
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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