Hydrochloric Acid → 2'-Allyloxy-4'-methoxyacetanilide

HRID 494921Notes

Reaction equation

HRID 494921 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].N1C=CC=CC=1.[CH2:14]([O:17][C:18]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:19]=1[NH2:20])[CH:15]=[CH2:16].Cl>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH2:14]([O:17][C:18]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:19]=1[NH:20][C:1](=[O:3])[CH3:2])[CH:15]=[CH2:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 576829162-Allyloxy-4-methoxyaniline

Product 1

HCID 576828282'-Allyloxy-4'-methoxyacetanilide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3 mg of 4-(dimethylamino)pyridine and 1 ml of acetic anhydride were successively added to 2 ml of pyridine containing 1.09 g of 2-allyloxy-4-methoxyaniline, and the reaction solution was then stirred at room temperature. After the disappearance of the raw material had been confirmed, 5 N HCl and ethyl acetate were added to the reaction solution, so as to separate an organic layer. The obtained organic layer was washed with a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. The residue was then solidified from t-butyl methyl ether-hexane, so as to obtain 1.04 g of the subject compound.

Workup

  1. customso as to separate an organic layer
  2. washThe obtained organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing the drying agent
  5. filtrationby filtration
  6. concentrationthe organic layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-1e88ac9d318b49719a5d5cdabb906013
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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