HCID 67328219, compound → HCID 67329151, compound

HRID 1853947Notes

Reaction equation

HRID 1853947 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][C:12]1=[O:18]>COC(OC)N(C)C>[CH3:3][N:11]([CH:16]=[C:13]1[C:14](=[O:17])[CH2:15][CH2:16][N:11]([C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[CH3:1])[C:12]1=[O:18])[CH3:12]

Participants

3

Reactant 1

HCID 67328219HCID 67328219, compound

Product 1

HCID 67329151HCID 67329151, compound

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

A solution of 1-(2-Methyl-5-nitro-phenyl)-piperidine-2,4-dione [100 mg, 0.402 mmol] in N,N-Dimethylformamide dimethyl acetal (DMA.DMF) [1 ml] was heated to reflux for 3 hrs. After cooling to room temperature, reaction mixture was concentrated under vacuum. The crude product obtained was further purified by silica gel chromatography using 30-60% ethylacetate/hexane as eluent to obtain pure desired product i.e., 3-Dimethylaminomethylene-1-(2-methyl-5-nitro-phenyl)-piperidine-2,4-dione [9] as dark red solid [Yield: 79.02 mg, 65.02%]

Workup

  1. temperatureto reflux for 3 hrs
  2. customreaction mixture
  3. concentrationwas concentrated under vacuum
  4. customThe crude product obtained
  5. customwas further purified by silica gel chromatography

Sources & evidence

ORD record
ord-3ea0e18ba4984cd9a7be6766b53f3450
Source dataset
uspto-grants-2015_02
Patent number
US08962637B2

Reaction notes

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