4-Methoxyphenylacetic Acid → HCID 22449691, compound

HRID 2187062Notes

Reaction equation

HRID 2187062 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]C(O)=O)=[CH:5][CH:4]=1.C([N:15]([CH2:18]C)CC)C.C1C=CC([O:26]P(OC2C=CC=CC=2)(N=[N+]=[N-])=O)=CC=1.[NH2:39][C:40]1[CH:49]=[CH:48][CH:47]=[C:42]([C:43]([O:45][CH3:46])=[O:44])[C:41]=1[C:50]([O:52]C)=O>C1(C)C=CC=CC=1>[O:26]=[C:18]1[N:15]([CH2:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:50](=[O:52])[C:41]2[C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:47][CH:48]=[CH:49][C:40]=2[NH:39]1

Participants

6

Reactant 4

HCID 76904-Methoxyphenylacetic AcidHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 13399384Dimethyl 3-aminobenzene-1,2-dicarboxylate

Product 1

HCID 22449691HCID 22449691, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Methoxyphenylacetic acid (11.5 g, 69.4 mmol) was suspended in toluene (200 ml) and then admixed sequentially with triethylamine (11.6 ml, 85.2 mmol) and diphenylphosphoric azide (17.9 ml, 85.2 mmol). The reaction mixture was stirred at room temperature for 1 hour, and then heated under ref lux for 3 hours. The mixture was combined with dimethyl 3-aminophthalate (13.1 g, 62.4 mmol) obtained in Reference Example 102 and then heated under reflux further for 20 hours. The solvent was distilled off under reduced pressure, and the residue was combined with water and extracted with ethyl acetate. After the extract was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure. The residue was subjected to a column chromatography on a silica gel eluted with n-hexane-ethyl acetate (10:1, v/v) to give the title compound (8.49 g, 40%) as a white crystal. This product was used in the next reaction without further purification.

Workup

  1. temperatureheated under ref lux for 3 hours
  2. customobtained in Reference Example 102
  3. temperatureheated
  4. temperatureunder reflux further for 20 hours
  5. distillationThe solvent was distilled off under reduced pressure
  6. extractionextracted with ethyl acetate
  7. washAfter the extract was washed with water
  8. dry with materialdried (MgSO4)
  9. distillationthe solvent was distilled off under reduced pressure
  10. washeluted with n-hexane-ethyl acetate (10:1

Sources & evidence

ORD record
ord-84ab5205a66347db8008d2077a225ad4
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

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