1-Amino-2-propanol → HCID 12384307, compound

HRID 1787861Notes

Reaction equation

HRID 1787861 reaction equation
[NH2:1][CH2:2][CH:3]([OH:5])[CH3:4].[C:6]1(=O)[O:11][C:9](=[O:10])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12.C(N(CC)CC)C.C1(C)C=CC=CC=1>O>[CH2:6]([O:11][C:9]([NH:1][CH2:2][CH:3]([OH:5])[CH3:4])=[O:10])[C:7]1[CH:8]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 41-Amino-2-propanolHCID 1140TolueneHCID 6811Phthalic AnhydrideHCID 8471Triethylamine

Product 1

HCID 12384307HCID 12384307, compoundYield 142.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a round bottom flask equipped with Dean-Stark trap was added (1) (2 g, 7.4 mmol), phthalic anhydride (1.1 g, 7.4 mmol), triethylamine (0.1 mL) and toluene (50 mL). The reaction mixture was heated to reflux and water produced was collected. After refluxing for 2 hours, the solvent was removed. The residue was acidified using 1 N HCl, filtered and washed with water, dried to give 2.2 g of (2). 1H NMR (DMSO-d6, 400 MHz): δ 7.8 (m, 4H), 7.3 (m, 5H), 7.1 (d, 2H), 6.8 (d, 2H), 5.05 (m, 1H), 3.3 (m, 2H).

Workup

  1. customTo a round bottom flask equipped with Dean-Stark trap
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. customwas collected
  5. temperatureAfter refluxing for 2 hours
  6. customthe solvent was removed
  7. filtrationfiltered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-2b99da6e97b8436a8959456d82cfddc4
Source dataset
uspto-grants-2009_03
Patent number
US07511063B2

Reaction notes

Loading…