Acetic Anhydride → HCID 68182233, compound

HRID 1620177Notes

Reaction equation

HRID 1620177 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([CH2:16][C:17]2[CH:18]=[N:19][C:20]3[C:25]([CH:26]=2)=[C:24]([O:27][CH3:28])[CH:23]=[CH:22][CH:21]=3)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:29](OC(=O)C)(=[O:31])[CH3:30]>CCOCC>[C:29]([C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH:11]([CH2:16][C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[C:24]([O:27][CH3:28])[CH:23]=[CH:22][CH:21]=2)[C:12]([O:14][CH3:15])=[O:13])(=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 68182212HCID 68182212, compound2×

Product 1

HCID 68182233HCID 68182233, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl 2-(3,4-dimethoxyphenyl)-3-(5-methoxyquinolin-3-yl)propanoate CCH 34144-5 (46 mg, 121 μmol) in acetic anhydride (2.0 mL, 21.2 mmol) at 0° C. in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added HClO4 (ca. 70% solution in water, 0.1 mL, 1.2 mmol). The reaction mixture was then allowed to warm up to RT, stirred for 45 min and diluted with Et2O (40 mL). The solid was filtered and washed several times with Et2O giving a brown residue. The residue was then suspended in CH2Cl2 (40 mL) before neutralisation with saturated aqueous NaHCO3 solution. The organic phase was isolated, washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 0:100) gave methyl 2-(2-acetyl-4,5-dimethoxyphenyl)-3-(5-methoxyquinolin-3-yl)propanoate CCH 34154 as a yellow solid (30 mg, 59% yield).

Workup

  1. filtrationThe solid was filtered
  2. washwashed several times with Et2O giving a brown residue
  3. customThe organic phase was isolated
  4. washwashed with brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated at 40° C. under vacuum
  8. customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 0:100)

Sources & evidence

ORD record
ord-45590504deb34ed8b58c7723cfb72509
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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