Phosphorus oxychloride → Methyl 3-chloro-7-fluoro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate

HRID 1403603Notes

Reaction equation

HRID 1403603 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=O)[C:8](=[O:21])[N:9]2[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:4][C:3]=1[C:23]([O:25][CH3:26])=[O:24].O=P(Cl)(Cl)[Cl:29]>>[Cl:29][C:7]1[C:8](=[O:21])[N:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C:10]2[C:5]([N:6]=1)=[CH:4][C:3]([C:23]([O:25][CH3:26])=[O:24])=[C:2]([F:1])[CH:11]=2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 70664935Methyl 7-fluoro-1-(4-methoxybenzyl)-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

Product 1

HCID 70665073Methyl 3-chloro-7-fluoro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylateYield 68%

Conditions

Temperature
130 °C

Procedure

Methyl 7-fluoro-1-(4-methoxybenzyl)-2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-carboxylate (35.0 g, 98 mmol) was added to POCl3 with stirring overnight at 130° C. and concentrated in vacuo. The product was precipitated via the addition of methanol (150 ml) and collected by filtration to afford methyl 3-chloro-7-fluoro-1-(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoxaline-6-carboxylate as a yellow solid (25.0 g, 68%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe product was precipitated via the addition of methanol (150 ml)
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-886021b2e93148aa814a83a381680986
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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