Water → Methyl 2-(9-bromo-2,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[1,2,3-de]quinoxalin-5-yl)acetate

HRID 862565Notes

Reaction equation

HRID 862565 reaction equation
O.[Br:2][C:3]1[CH2:4][CH:5]2[C:10](=[C:11]([N+:13]([O-])=O)[CH:12]=1)[N:9]([C:16]([C:18](OCC)=[O:19])=[O:17])[CH:8]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH2:7][CH2:6]2>CC(C)=O.[Cl-].[Cl-].[Cl-].[Ti+3]>[Br:2][C:3]1[CH:4]=[C:5]2[CH2:6][CH2:7][CH:8]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[N:9]3[C:16](=[O:17])[C:18](=[O:19])[NH:13][C:11]([CH:12]=1)=[C:10]23

Participants

5

Reactant 2

HCID 962WaterHCID 676513916-Bromo-2-methoxycarbonylmethyl-8-nitro-N-ethoxalyltetrahydroquinoline

Product 1

HCID 10066635Methyl 2-(9-bromo-2,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[1,2,3-de]quinoxalin-5-yl)acetateYield 82.4%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 180AcetoneSolvent2×

Procedure

To a mixture of 20% aqueous titanium trichloride (670 g, 0.867 mol), water (500 mL), and acetone (500 mL) was added dropwise a solution of 6-bromo-2-methoxycarbonylmethyl-8-nitro-N-ethoxalyltetrahydroquinoline (52.0 g, 0.121 mol) in acetone (600 mL) at 0° C. The mixture was stirred overnight at room temperature, concentrated to ca. 1 L and diluted with water (1 L). The precipitates formed were collected by filtration, washed with water, and dried in vacuo to give 35.2 g of the title compound. The filtrate was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with ethyl acetate to give 6.0 g of the title compound (total 89%).

Workup

  1. concentrationconcentrated to ca. 1 L
  2. additiondiluted with water (1 L)
  3. customThe precipitates formed
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-9706aff33d5a4a269e55f20a01147ccc
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

Loading…