Homophthalic anhydride → HCID 58158002, compound

HRID 1255511Notes

Reaction equation

HRID 1255511 reaction equation
[C:1]1(=[O:12])[O:7][C:5](=O)[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1.[CH2:13]([NH2:17])[CH2:14][CH:15]=[CH2:16]>C1(C)C=CC=CC=1.C(Cl)Cl>[CH2:13]([N:17]1[C:1](=[O:12])[CH2:2][C:3]2[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5]1=[O:7])[CH2:14][CH:15]=[CH2:16]

Participants

5

Reactant 2

HCID 12801Homophthalic anhydrideHCID 4437323-Buten-1-amine

Product 1

HCID 58158002HCID 58158002, compoundYield 37.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
160 °C

Procedure

Homophthalic anhydride (1.5 g, 9.25 mmol), 3-buten-1-amine (1.129 ml, 11.10 mmol), and 4 A molecular sieves (300 mg) were combined in toluene (15 ml) and heated to 160° C. in a microwave for 40 minutes. The reaction mixture was diluted with CH2Cl2 and the slurry was filtered over CELITE. The filtrate was concentrated in vacuo and the resulting residue was purified by column chromatography (gradient elution, 10-20% EtOAc/Hexane) to afford the title compound (0.75 g, 36%) as an oil. LCMS (ES+) m/z 216.03 (M+H)+.

Workup

  1. filtrationthe slurry was filtered over CELITE
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe resulting residue was purified by column chromatography (gradient elution, 10-20% EtOAc/Hexane)

Sources & evidence

ORD record
ord-701588af5d0d4b6abc73b058575ab3f4
Source dataset
uspto-grants-2013_06
Patent number
US08461107B2

Reaction notes

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