Water → 9-Bromo-5-iodomethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52493Notes

Reaction equation

HRID 52493 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17]OS(C)(=O)=O)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[I-:23].[Na+].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][I:23])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 542445079-Bromo-5-methylsulfonyloxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 544452219-Bromo-5-iodomethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 78.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 9-bromo-5-methylsulfonyloxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (2.3 g, 5.91 mmol) and sodium iodide (7.9 g, 52.7 mmol) in DMF (30 mL) was heated at 60° C. for 22 h and poured into water (400 mL). The precipitates formed was collected by filtration, washed with water, and dried in vacuo to give 1.95 g of the title compound (78%): mp 260°~270.5° C.; 1H NMR (270 MHz, CD3OD) δ7.22 (s, 1H), 7.19 (s, 1H), 4.95~5.07 (m, 1H), 3.50 (dd, 1H, J=10.2, 4 Hz), 3.24 (d, 1H, J=10.2 Hz), 2.97 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.84 (dm, 1H, J=17.1 Hz), 2.70 (dm, 1H, J=13.5 Hz), 1.90~2.07 (m, 1H).

Workup

  1. customThe precipitates formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-8b2ba830521e40fcb19103cc7afb9b02
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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