Anthranilic Acid → HCID 823661, compound

HRID 1828749Notes

Reaction equation

HRID 1828749 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4]>C(OC(=O)CCC)(=O)CCC>[CH2:2]([C:1]1[O:9][C:1](=[O:10])[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[N:4]=1)[CH2:8][CH3:7]

Participants

3

Reactant 1

HCID 227Anthranilic Acid

Product 1

HCID 823661HCID 823661, compound

Reagents, catalysts & solvents 1

HCID 7798Butyric anhydrideSolvent

Procedure

A solution of anthranilic acid (3.40 g, 25.0 mmol) in butyric anhydride (10 mL) was heated at 150° C. for 1 hOUR. The bath temperature was lowered to 90° C. and the excess butyric anhydride was removed by distillation. The residue was distilled to provide 2-propyl-4H-3,1-benzoxazin-4-one (1—1) as a colorless liquid (bp 110–112° C./2 mm Hg), which solidified upon standing. 1H NMR (500 MHz, CDCl3) δ8.19 (d, 1H, J=8 Hz, 1H), 7.80 (t, J=7 Hz, 1H), 7.57 (d, J=8 Hz, 1H), 7.50 (t, J=7 Hz, 1H), 2.68 (t, J=7 HZ, 2H), 1.87 (m, 2H), 1.05 (t, J=7 Hz, 3H).

Workup

  1. customwas lowered to 90° C.
  2. customthe excess butyric anhydride was removed by distillation
  3. distillationThe residue was distilled

Sources & evidence

ORD record
ord-b2462cc693e743d19acf9ee5988b0431
Source dataset
uspto-grants-2006_06
Patent number
US07060705B2

Reaction notes

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