Acetic Acid → HCID 67206341, compound

HRID 1023856Notes

Reaction equation

HRID 1023856 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6].[C:11]1(=O)[O:16][C:14](=[O:15])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.C(O)(=O)C>O>[OH:6][CH2:5][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[N:1]1[C:14](=[O:15])[C:13]2[C:12](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]1=[O:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6811Phthalic AnhydrideHCID 79282o-Aminophenethyl alcohol

Product 1

HCID 67206341HCID 67206341, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A flask containing 2-aminophenethyl alcohol (565 mg, 4.12 mmol), phthalic anhydride (641 mg, 4.32 mmol) and acetic acid (4 mL) was heated at 100° C. for 1 h. The reaction mixture was poured into water (30 mL) and the solid was filtered off and the solids were washed with water. The crude was purified by flash column chromatography to afford the desired product as white solid (435 mg, 1.63 mmol, 40%). 1H NMR: 1.79 (br s, 1H), 2.78 (t, 2H, J=6.4 Hz), 3.81 (t, 2H, J=6.4 Hz), 7.20 (d, 1H, J=8 Hz), 7.36-7.41 (m, 1H), 7.46 (d, 2H, J=4 Hz), 7.79-7.83 (m, 2H), 7.94-7.97 (m, 21-1).

Workup

  1. filtrationthe solid was filtered off
  2. washthe solids were washed with water
  3. customThe crude was purified by flash column chromatography

Sources & evidence

ORD record
ord-9252dc76a0bc4eec821ab2b4978b57de
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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