Phthalic Anhydride → HCID 519849, compound

HRID 2402287Notes

Reaction equation

HRID 2402287 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1>C(O)(=O)C>[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][N:19]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 754524-Methoxybenzylamine

Product 1

HCID 519849HCID 519849, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of phthalic anhydride (10 g, 0.067 mmol) and 4-methoxybenzylamine (9.7 ml, 0.074) in glacial acetic acid (60 ml) was stirred in a 90° C. oil bath for 2½ hr, cooled to room temperature and the excess acetic acid removed under reduced pressure. The residual mixture was diluted with water (50 ml) and poured slowly into a saturated NaHCO3 solution (150 ml). The mixture was stirred at room temperature overnight and the precipitate collected by filtration, rinsing further with water. The precipitate was then dried under reduced pressure to provide a white solid product (15.7 g) 87%.

Workup

  1. temperaturecooled to room temperature
  2. customthe excess acetic acid removed under reduced pressure
  3. additionThe residual mixture was diluted with water (50 ml)
  4. additionpoured slowly into a saturated NaHCO3 solution (150 ml)
  5. stirringThe mixture was stirred at room temperature overnight
  6. filtrationthe precipitate collected by filtration
  7. washrinsing further with water
  8. customThe precipitate was then dried under reduced pressure

Sources & evidence

ORD record
ord-72f52bd2759546d4a1eca6af72bfb3c7
Source dataset
uspto-grants-2014_08
Patent number
US08796313B2

Reaction notes

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