Tetrahydrofuran → 5-Amino-1,3-dimethyl-1,2-dihydropyridin-2-one

HRID 873819Notes

Reaction equation

HRID 873819 reaction equation
[CH3:1][N:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH3:11])[C:3]1=[O:12].C1COCC1>[Pd].CO>[NH2:8][C:6]1[CH:5]=[C:4]([CH3:11])[C:3](=[O:12])[N:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 46575261,3-dimethyl-5-nitropyridin-2(1H)-one

Product 1

HCID 674566165-Amino-1,3-dimethyl-1,2-dihydropyridin-2-oneYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1,3-dimethyl-5-nitropyridin-2(1H)-one (Step 20.1) (16.4 g, 98 mmol), Pd/C 10% (2.0 g), THF (200 mL) and MeOH (200 mL) was stirred for 3 hr at rt under a hydrogen atmosphere (0.1 bar). The reaction mixture was filtered over celite and concentrated. The crude material was purified by chromatography (CH2Cl2/MeOH/NH3 98/1/1) to afford the title product (10.3 g, 70.8 mmol, 73% yield) as a green oil. The green oil was triturated in diethyl ether to afford a powder. tR: 0.21 min (LC-MS 2); ESI-MS: 139 [M+H]+ (LC-MS 2); Rf=0.35 (CH2Cl2/MeOH 9:1).

Workup

  1. filtrationThe reaction mixture was filtered over celite and
  2. concentrationconcentrated
  3. customThe crude material was purified by chromatography (CH2Cl2/MeOH/NH3 98/1/1)

Sources & evidence

ORD record
ord-400bc6a2d45b4483b34280f73da11e23
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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