Acetyl chloride → HCID 59443454, compound

HRID 1035622Notes

Reaction equation

HRID 1035622 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=3)[CH:11]=2)[CH:7]=[CH:6][C:4]=1[NH2:5].[C:22](Cl)(=[O:24])[CH3:23].CN(C1C=CC=CN=1)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:9]=[C:8]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=3)[CH:11]=2)[CH:7]=[CH:6][C:4]=1[NH:5][C:22](=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 218852-DimethylaminopyridineHCID 59443493HCID 59443493, compound

Product 1

HCID 59443454HCID 59443454, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methoxy-4-(6-methoxy-2-naphthyl)aniline (140 mg, 0.50 mmol, 1 eq) in 20 ml of dry dichloromethane are added acetyl chloride (64 μl, 71 mg, 0.91 mmol, 1.8 eq) and trace amounts of DMAP (dimethylaminopyridine). After stirring for 18 h at RT, the reaction mixture is stopped by adding a 2% sodium carbonate solution, the phases are separated, and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and concentrated in vacuum on a rotary evaporator. Purification by column chromatography with a gradient of dichloromethane/methanol 10/0 to 9.8/0.2 yielded the desired product in a yield of 66%, 108 mg.

Workup

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted with dichloromethane
  3. dry with materialThe combined organic phases are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum on a rotary evaporator
  6. customPurification by column chromatography with a gradient of dichloromethane/methanol 10/0 to 9.8/0.2

Sources & evidence

ORD record
ord-ad8bb9d76f964144ae9eb56c9449591f
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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