Ethyl Acetate → HCID 58149933, compound

HRID 2192466Notes

Reaction equation

HRID 2192466 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH:19]=[CH:20][N+:21]([O-])=[CH:22]4)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Cl[C:29]1C=CC2C(=CC=CC=2)N=1.[C:39]([O:42][CH2:43][CH3:44])(=[O:41])[CH3:40]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:18]=3[CH:19]=[CH:20][N:21]=[C:22]4[CH2:29][CH2:40][C:39]([O:42][CH2:43][CH3:44])=[O:41])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 119282-ChloroquinolineHCID 66877400HCID 66877400, compound

Product 1

HCID 58149933HCID 58149933, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The contents of the three vials were pooled with the reaction mixture from a previous preparation of D6 (using the same method and 100 mg of chloroquinoline starting material), and the mixture diluted with ethyl acetate and washed sequentially with brine (×2) and water (×2). The organic layers were concentrated in vacuo to give a red oil that was dissolved in dichloromethane, and purified by flash chromatography on silica gel, eluting with a dichloromethane/ethyl acetate (2% to 20% EtOAc) gradient. The relevant fractions were pooled and concentrated in vacuo to give a red solid that was triturated with diethyl ether. The resulting brick coloured solid was collected by filtration and dried in vacuo to give the title compound (80 mg, 8%).

Workup

  1. washwashed sequentially with brine (×2) and water (×2)
  2. concentrationThe organic layers were concentrated in vacuo
  3. customto give a red oil that
  4. custompurified by flash chromatography on silica gel
  5. washeluting with a dichloromethane/ethyl acetate (2% to 20% EtOAc) gradient
  6. concentrationconcentrated in vacuo
  7. customto give a red solid that
  8. customwas triturated with diethyl ether
  9. filtrationwas collected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-d707b9979b0e4a46be77afaaac5660dd
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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