4,5-Dichlorophthalic anhydride → HCID 9865397, compound

HRID 1451864Notes

Reaction equation

HRID 1451864 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=O)[C:5]2=[CH:11][C:12]=1[Cl:13].[NH2:14][CH:15]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[CH2:16][C:17]([OH:19])=[O:18]>C(O)(=O)C>[Cl:13][C:12]1[CH:11]=[C:5]2[C:6](=[O:8])[N:14]([CH:15]([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[CH2:16][C:17]([OH:19])=[O:18])[C:9](=[O:10])[C:4]2=[CH:3][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 703344,5-Dichlorophthalic anhydrideHCID 5858893-Amino-3-(4-methoxyphenyl)propanoic acid

Product 1

HCID 9865397HCID 9865397, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4.5-dichlorophthalic anhydride (0.91, 4.19 mmol) and 3-amino-3-(4'-methoxyphenyl) propionic acid in 10 mL acetic acid was stirred under nitrogen for 6 hours. The reaction was cooled and removed some of the solvent. The slurry was filtered and the solid was dried to afford 1.20 g (61%) of 3-(4',5'-dichlorophthalimido)-3-(4'-methoxyphenyl)propionic acid as a white powder. mp 182°-185° C.; 1H NMR (DMSO-d6, 250 MHz) δ 8.19 (s, 2H), 7.34 (d, 2 H, J=8.7), 6.90 (d, 2H, J=8.7), 5.61 (t, 1H, J=7.8), 3.72 (s, 3H), 3.50-3.20 (m, 2H). 13C NMR (DMSO-d6) δ 171.6, 165.8, 158.8, 137.6, 131.0, 130.4, 128.4, 125.4, 113.9, 55.1, 50.0, 35.8. Anal. Calcd for C18H14N2O7. Theoretical: pending

Workup

  1. temperatureThe reaction was cooled
  2. customremoved some of the solvent
  3. filtrationThe slurry was filtered
  4. customthe solid was dried

Sources & evidence

ORD record
ord-30b7e9739611453e9d9542e5465dc377
Source dataset
uspto-grants-1997_02
Patent number
US05605914

Reaction notes

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