2-Methoxyaniline → Acetoacet-o-anisidide

HRID 259965Notes

Reaction equation

HRID 259965 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[CH2:10]=[C:11]1[O:15][C:13](=[O:14])[CH2:12]1>C(O)C>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH:5][C:13](=[O:14])[CH2:12][C:11]([CH3:10])=[O:15]

Participants

4

Reactant 2

HCID 70002-MethoxyanilineHCID 12661Diketene

Product 1

HCID 7078Acetoacet-o-anisidide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

2.4 kg/h (19.5 mol/h) of 2-methoxyaniline, 1.98 kg/h (23.1 mol/h) of diketene (purity 98%) and 6.9 kg/h of aqueous 30% strength ethanol are reacted separately but simultaneously as described in Example 1. The product stream of about 0.3 l, produced under reflux at about 85° C. and kept to a constant volume by pumping out, is cooled down to about 15° C., and the reaction product is crystallized out and separated from the 5.8 kg/h of mother liquor by filtration. The light-colored solids are washed with 5.8 kg/h of aqueous 30% strength ethanol and dried, leaving 3.8 kg/h (18.3 mol/h) of 2'-methoxyacetoacetanilide, corresponding to 94% of yield based on amine. The purity of the product is better than 99.5%.

Workup

  1. customThe product stream of about 0.3 l, produced
  2. temperatureis cooled down to about 15° C.
  3. customthe reaction product is crystallized out
  4. customseparated from the 5.8 kg/h of mother liquor by filtration
  5. washThe light-colored solids are washed with 5.8 kg/h of aqueous 30% strength ethanol
  6. customdried

Sources & evidence

ORD record
ord-7a17fb4e4682420d8fa59c58a58b72ad
Source dataset
uspto-grants-1996_06
Patent number
US05523486

Reaction notes

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