Hydrochloric Acid → HCID 67770344, compound

HRID 373775Notes

Reaction equation

HRID 373775 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[Cl:13])[NH:9][C:8](=[O:14])[CH:7]=[N:6]2.Br[CH:16]([CH2:22][CH2:23][CH2:24][CH3:25])[C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl>C(O)C>[CH2:20]([O:19][C:17]([CH2:16][CH2:22][CH2:23][CH2:24][CH2:25][N:9]1[C:10]2[C:5](=[CH:4][C:3]([Cl:2])=[C:12]([Cl:13])[CH:11]=2)[N:6]=[CH:7][C:8]1=[O:14])=[O:18])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79072Ethyl 2-bromohexanoateHCID 5360545SodiumHCID 144236366,7-Dichloroquinoxalin-2(1H)-one

Product 1

HCID 67770344HCID 67770344, compoundYield 10.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere sodium (0.148 g, 6.42 mmol) was dissolved in 50 ml of abs. ethanol and 6,7-dichloroquinoxalin-2(1H)-one (1.20 g, 5.58 mmol) (Liebigs Ann. Chem., (1982), 754) was added. The mixture was stirred until the compound dissolved, and ethyl 2-bromohexanoate (1.30 ml, 7.1 mmol) was added. The reaction mixture was refluxed for 72 h, cooled to room temperature, then poured onto crushed ice and acidified by dilute hydrochloric acid (pH=2). The precipitated compound was extracted with ethyl acetate and purified by column chromatography on silica gel (eluent 15% THF in heptane) to afford 0,21 g of 1-((1-ethoxycarbonyl)pentyl)-6,7-dichloroquinoxalin-2(1H)-one 1H-NMR(DMSO-d6):δ 0.78(t, 3H), 1.1(t, 3H), 1.15-1.35(m, 4H), 2.0-2.25(m, 2H), 4.02-4.18(m, 2H), 5.58-5.75(m, 1H), 8.02-8.36(broad, 1H), 8.18(s, 1H), 8.33(s, 1H).

Workup

  1. dissolutiondissolved
  2. temperatureThe reaction mixture was refluxed for 72 h
  3. additionpoured
  4. customonto crushed ice
  5. extractionThe precipitated compound was extracted with ethyl acetate
  6. custompurified by column chromatography on silica gel (eluent 15% THF in heptane)

Sources & evidence

ORD record
ord-6afe7c461ef34a2fa6c9a9c3277b3e9a
Source dataset
uspto-grants-1992_11
Patent number
US05166155

Reaction notes

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