Acetic Acid → 1-(2-Bromo-5-methoxyphenylamino)-1,5-dioxohex-3-en-3-yl acetate

HRID 1627916Notes

Reaction equation

HRID 1627916 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:3]=1[NH2:4].[C:11]([O:14][C:15]1[CH2:16][C:17](=[O:22])O[C:19](=[O:21])[CH:20]=1)(=[O:13])[CH3:12].[C:23](O)(=O)C>>[C:11]([O:14][C:15](=[CH:20][C:19](=[O:21])[CH3:23])[CH2:16][C:17]([NH:4][C:3]1[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:2]=1[Br:1])=[O:22])(=[O:13])[CH3:12]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 7930162-Bromo-5-methoxyanilineHCID 124390722,6-dioxo-3,6-dihydro-2H-pyran-4-yl acetate

Product 1

HCID 666038371-(2-Bromo-5-methoxyphenylamino)-1,5-dioxohex-3-en-3-yl acetateYield 71%

Conditions

Temperature
35 °C

Procedure

2-bromo-5-methoxyaniline (6 g; 29.7 mmol) was dissolved in acetic acid (33.7 ml) and 2,6-dioxo-3,6-dihydro-2H-pyran-4-yl acetate (4.59 g; 27.0 mmol) was added. The reaction was stirred at 35° C. in a sand bath for 2 h. The reaction was quenched by adding ice-water (250 ml), the precipitate formed was filtered, washed with water and dried over phosphorus pentoxide under reduced pressure to afford 8.98 g (71%) of 1-(2-bromo-5-methoxyphenylamino)-1,5-dioxohex-3-en-3-yl acetate as a grey solid.

Workup

  1. customThe reaction was quenched
  2. additionby adding ice-water (250 ml)
  3. customthe precipitate formed
  4. filtrationwas filtered
  5. washwashed with water
  6. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-2045ba4f11674bc2805ccb5c759eba2a
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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