N,N-Dimethylaniline → HCID 68194043, compound

HRID 1520134Notes

Reaction equation

HRID 1520134 reaction equation
O=P(Cl)(Cl)[Cl:3].CN(C)C1C=CC=CC=1.[CH3:15][O:16][C:17]1[CH:39]=[CH:38][C:20]([CH2:21][N:22]2[C:31]3[C:26](=[CH:27][C:28]([C:32]([O:34][CH3:35])=[O:33])=[CH:29][CH:30]=3)[NH:25][C:24](=O)[C:23]2=[O:37])=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[Cl:3][C:24]1[C:23](=[O:37])[N:22]([CH2:21][C:20]2[CH:38]=[CH:39][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)[C:31]2[C:26]([N:25]=1)=[CH:27][C:28]([C:32]([O:34][CH3:35])=[O:33])=[CH:29][CH:30]=2

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 68194123HCID 68194123, compound

Product 1

HCID 68194043HCID 68194043, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

POCl3 (2 g, 13.25 mmol) and N,N-dimethylbenzenamine (2.13 g, 17.60 mmol,) were added to a solution of methyl 1-(4-methoxybenzyl)-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate (3 g, 8.81 mmol) in toluene (100 ml). The resulting reaction was stirred overnight at 110° C. and concentrated in vacuo. The residue was triturated with methanol (50 ml) and collected by filtration to afford methyl 3-chloro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a green solid (2.27 g, 72%).

Workup

  1. customThe resulting reaction
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with methanol (50 ml)
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-af4dc05d217f4738aacf5efeef4bcebf
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

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