Formaldehyde → 4-oxo-4H-3,1-benzoxazine-8-carboxylic acid

HRID 1842856Notes

Reaction equation

HRID 1842856 reaction equation
[NH2:1][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:14]=O>>[O:5]=[C:4]1[C:3]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]([OH:13])=[O:12])[C:2]=2[N:1]=[CH:14][O:6]1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 2929162-Aminoisophthalic acid

Product 1

HCID 676086644-oxo-4H-3,1-benzoxazine-8-carboxylic acidYield 89%

Conditions

Temperature
140 °C

Procedure

2-Aminoisophthalic acid moiety (50.0 g; 276.0 mmol) and formaldehyde (250.0 ml; 5.00 V) were combined and heated to 140° C. for 4 h. The reaction mixture was cooled to room temperature and distilled under high vacuum on the rotary evaporator. The remaining formaldehyde was removed by azeotropic distillation with toluene. The residue was slurried with ethyl ether, filtered, and the solid was dried under vacuum to provide the desired intermediate (50.3 g, 89% yield).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. distillationdistilled under high vacuum on the rotary evaporator
  3. customThe remaining formaldehyde was removed by azeotropic distillation with toluene
  4. filtrationfiltered
  5. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-aa8514ff7c944df383ff18272029e126
Source dataset
uspto-grants-2015_02
Patent number
US08946247B2

Reaction notes

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