3-Nitrophthalic anhydride → HCID 9864149, compound

HRID 1421313Notes

Reaction equation

HRID 1421313 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=12)=O)([O-:3])=[O:2].[NH2:15][CH:16]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)[CH2:17][C:18]([OH:20])=[O:19]>C(O)(=O)C>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([CH:16]([N:15]2[C:10](=[O:11])[C:5]3=[C:4]([N+:1]([O-:3])=[O:2])[CH:14]=[CH:13][CH:12]=[C:6]3[C:7]2=[O:9])[CH2:17][C:18]([OH:20])=[O:19])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 216313-Nitrophthalic anhydrideHCID 5858893-Amino-3-(4-methoxyphenyl)propanoic acid

Product 1

HCID 9864149HCID 9864149, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-nitrophthalic anhydride (1.54, 8.0 mmol) and 3-amino-3-(4-methoxyphenyl)propionic acid (1.56 g, 8.0 mmol) in 15 mL of acetic acid was refluxed for 3.5 h under nitrogen. The reaction was cooled and removed some of the solvent. The slurry was filtered and the solid was dried to afford 2.34 g (79%) of 3-(4-methoxyphenyl)-3-(3-nitrophthalimido)propionic acid as a white powder: mp 178-180° C.; 1H NMR (DMSO-d6, 250 MHz)δ 8.07-8.02 (m, 3H), 7.38 (d, 2H, J=8.7), 6.90 (d, 2H, J=8.7, 5.68-5.07 (m, 1H), 3.72 (s, 3H), 3.48-3.22 (m, 2H); 13C NMR (DMSO-d6)δ 171.6, 165.7, 163.0, 158.8, 144.4, 136.4, 133.0, 130.2, 128.6, 128.5, 127.0, 122.4, 113.9, 55.1, 50.0, 35.8. Anal. Calcd for C18H14N2O7. Theoretical: C, 58.38; H, 3.81; N, 7.56. Found: C, 58.18; H, 3.79; N, 7.36.

Workup

  1. temperaturewas refluxed for 3.5 h under nitrogen
  2. temperatureThe reaction was cooled
  3. customremoved some of the solvent
  4. filtrationThe slurry was filtered
  5. customthe solid was dried

Sources & evidence

ORD record
ord-ac6beef413cb4830986b3859084e9004
Source dataset
uspto-grants-2000_06
Patent number
US06075041

Reaction notes

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