Homophthalic anhydride → 2-[2-Oxo-2-[[(1S)-1-phenylpropyl]amino]ethyl]benzoic acid

HRID 884739Notes

Reaction equation

HRID 884739 reaction equation
[C:1]1(=[O:12])[O:7][C:5](=[O:6])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]2[CH2:2]1.[C:13]1([C@@H:19]([NH2:22])[CH2:20][CH3:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[C:13]1([C@@H:19]([NH:22][C:1]([CH2:2][C:3]2[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=2[C:5]([OH:7])=[O:6])=[O:12])[CH2:20][CH3:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 12801Homophthalic anhydrideHCID 6993773(1S)-1-phenylpropan-1-amine

Product 1

HCID 577332512-[2-Oxo-2-[[(1S)-1-phenylpropyl]amino]ethyl]benzoic acidYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of homophthalic anhydride (810 mg, 5 mmol) and (S)-(−)-1-phenylpropylamine (676 mg, 5 mmol) in acetonitrile (15 ml) was heated under microwave irradiation at +150° C. for 15 min. White precipitate was collected by filtration, washed with heptane and dried in vacuo to give pure title compound in 72% yield (1.065 g). Alternatively, to a stirred solution of homophthalic anhydride (16.214 g, 0.1 mol) in acetonitrile (100 ml) (S)-(−)-1-phenylpropylamine (13.83 g, 0.102 mol) was added dropwise (exothermic reaction) and the obtained reaction mixture was refluxed for 5 min. It was allowed to cool and the product was isolated by filtration as above to give 23.4 g of colourless solid, 79% yield. LC-MS (m/z) 298.5 (MH+); tR=1.11. 1H NMR (500 MHz, DMSO-d6): 0.84 (t, J=7.3 Hz, 3H), 1.67 (quintet, J=7.3 Hz, 2H), 3.85 (d of AB system, J=15.1 Hz, 1H), 3.95 (d of AB system, J=15.1 Hz, 1H), 4.66 (q, J=7.6 Hz, 1H), 7.2 (unres. m, 1H), 7.25-7.34 (m, 5H), 7.45 (t, J=7.3 Hz, 1H), 7.8 (d, J=7.8 Hz, 1H), 8.39 (br. d, J=7.7 Hz, 1H, NH).

Workup

  1. temperaturewas heated under microwave irradiation at +150° C. for 15 min
  2. filtrationWhite precipitate was collected by filtration
  3. washwashed with heptane
  4. customdried in vacuo

Sources & evidence

ORD record
ord-193f083ec4c4402ea2e9e0937e176121
Source dataset
uspto-grants-2012_08
Patent number
US08242134B2

Reaction notes

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