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

HRID 52566Notes

Reaction equation

HRID 52566 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][OH:18])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(O)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH:17]=[O:18])[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 702EthanolHCID 159087TriacetoxyperiodinaneHCID 544705519-bromo-5-hydroxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 541235619-Bromo-5-formyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dioneYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 9-bromo-5-hydroxymethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (520 mg, 1.67 mmol) and Dess-Martin periodinane (945 mg, 2.27 mmol) in THF (140 mL) was stirred for 5 h at room temperature. The excess reagent was decomposed by addition of ethanol and the resulting mixture was concentrated. The residual solids were triturated with dichloromethane and the insoluble materials were removed by filtration. The filtrate was concentrated and the residue was purified by silica gel column chromatography with 0.2% acetic acid/ethyl acetate to give 330 mg of the title compound (64%): 1H NMR (270 MHz, DMSO-d6) δ12.30 (bs, 1H), 9.57 (s, 1H), 7.21 (d, 1H, J=2 Hz), 7.19 (d, 1H, J=2 Hz), 5.31~5.37 (m, 1H), 2.85 (dm, 1H, J=15.8 Hz), 2.45~2.68 (m, 2H), 1.92~2.10 (m, 1H).

Workup

  1. concentrationthe resulting mixture was concentrated
  2. customThe residual solids were triturated with dichloromethane
  3. customthe insoluble materials were removed by filtration
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel column chromatography with 0.2% acetic acid/ethyl acetate

Sources & evidence

ORD record
ord-c60d274ab3874b76b38e5aae956c3dc9
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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