Itaconic acid → 5-Oxo-1-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)pyrrolidin-3-carboxylic acid

HRID 1846992Notes

Reaction equation

HRID 1846992 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.[C:13]([OH:21])(=[O:20])[C:14]([CH2:16][C:17](O)=[O:18])=[CH2:15]>O>[O:18]=[C:17]1[N:1]([C:2]2[CH:3]=[CH:4][C:5]3[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=3[CH:12]=2)[CH2:15][CH:14]([C:13]([OH:21])=[O:20])[CH2:16]1

Participants

4

Reactant 2

HCID 811Itaconic acidHCID 27636816-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 867249245-Oxo-1-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)pyrrolidin-3-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-amino-2H-1,4-benzoxazin-3(4H)-one (4.93 g, 30.0 mmol), itaconic acid (4.06 g, 31.2 mmol) and water (80 ml) was heated under reflux overnight. The reaction solution was cooled, and the insoluble material was collected by filtration and washed with water and diethyl ether. The filtrate was dried at 50° C. under reduced pressure to yield 7.92 g (96%) of the title compound in the form of a brownish solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. temperatureThe reaction solution was cooled
  4. filtrationthe insoluble material was collected by filtration
  5. washwashed with water and diethyl ether
  6. customThe filtrate was dried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-11322bb82aaf49388cc2a6261866a1e3
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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