Sulfuric Acid → 2-(8-Bromo-5-methoxy-2-oxo-1,2-dihydroquinolin-4-yl)acetic acid

HRID 1627917Notes

Reaction equation

HRID 1627917 reaction equation
C(O[C:5](=[CH:19][C:20](=[O:22])C)[CH2:6][C:7]([NH:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[Br:18])=[O:8])(=O)C.S(=O)(=O)(O)[OH:24]>>[Br:18][C:11]1[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[C:15]2[C:10]=1[NH:9][C:7](=[O:8])[CH:6]=[C:5]2[CH2:19][C:20]([OH:22])=[O:24]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 666038371-(2-Bromo-5-methoxyphenylamino)-1,5-dioxohex-3-en-3-yl acetate

Product 1

HCID 595785222-(8-Bromo-5-methoxy-2-oxo-1,2-dihydroquinolin-4-yl)acetic acidYield 89%

Procedure

1-(2-bromo-5-methoxyphenylamino)-1,5-dioxohex-3-en-3-yl acetate (8 g; 21.50 mmol) was added in small portions to concentrated sulfuric acid (30 ml) at room temperature and the mixture was stirred for 30 min. Ice was added to the reaction mixture and the formed precipitate was filtered, washed with water and dried over phosphorus pentoxide under reduced pressure to afford 5.97 g (89%) of 2-(8-bromo-5-methoxy-2-oxo-1,2-dihydroquinolin-4-yl)acetic acid as a grey solid.

Workup

  1. additionIce was added to the reaction mixture
  2. filtrationthe formed precipitate was filtered
  3. washwashed with water
  4. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-d3545e2bbf314f74995444c24f0a0f30
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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