Anthranilic Acid → HCID 22320187, compound

HRID 498001Notes

Reaction equation

HRID 498001 reaction equation
[OH:1][CH:2]([CH2:14][CH3:15])[CH:3]=[C:4]1C(=O)OC(C)(C)OC1=O.CC1(C)OC(=O)CC(=O)O1.C(Cl)(=O)CC.[C:31]([OH:40])(=[O:39])[C:32]1[C:33](=[CH:35][CH:36]=[CH:37][CH:38]=1)[NH2:34].C(OC(=O)C)(=O)C>C1C=CC=CC=1.O1CCCC1.CC(C)=O>[O:1]=[C:2]([CH2:14][CH3:15])[CH2:3][C:4]1[O:39][C:31](=[O:40])[C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=1

Participants

9

Reactant 5

HCID 227Anthranilic AcidHCID 7918Acetic AnhydrideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 62324Propionyl chlorideHCID 22320408HCID 22320408, compound

Product 1

HCID 22320187HCID 22320187, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution in a mixture of benzene (100 mL)/acetone (100 mL) of the crude 5-(2-hydroxybutylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione which was previously prepared from Meldrum's acid (57.7 g, 0.40 mol) and propionyl chloride(37.0 g, 0.40 mol) according to the methods described in Synthesis, p. 1213 (1992) and Org. Synth., vol. 63, p. 198 (1985), anthranilic acid (45.8 g, 0.33 mol) was added and the mixture was heated under reflux for 3 hours. The solution was cooled to room temperature and concentrated under reduced pressure. The residue was suspended in a mixture of acetic anhydride (68.1 g, 0.667 mol) and tetrahydrofuran (150 mL), and the suspension was heated under reflux for 30 minutes. The solution was cooled to room temperature and concentrated under reduced pressure, and the residue thus obtained was purified by silica gel column chromatography (ethyl acetate:hexane=2:8) to give the title compound (28.4 g, 33% yield).

Workup

  1. customdescribed in Synthesis, p
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. concentrationconcentrated under reduced pressure
  5. temperaturethe suspension was heated
  6. temperatureunder reflux for 30 minutes
  7. temperatureThe solution was cooled to room temperature
  8. concentrationconcentrated under reduced pressure
  9. customthe residue thus obtained
  10. customwas purified by silica gel column chromatography (ethyl acetate:hexane=2:8)

Sources & evidence

ORD record
ord-0e4e39d2c052427da76e5ffc44a07bda
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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