Neopentyl glycol → HCID 86686023, compound

HRID 2277728Notes

Reaction equation

HRID 2277728 reaction equation
[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7](=[O:12])[C:6]=2[CH:5]=[N:4][CH:3]=1.[CH3:13][C:14]([CH3:19])([CH2:17]O)[CH2:15][OH:16]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7]3([O:16][CH2:15][C:14]([CH3:19])([CH3:17])[CH2:13][O:12]3)[C:6]=2[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 31344Neopentyl glycolHCID 717433804-Bromo-6,7-dihydro-8(5H)-isoquinolinone

Product 1

HCID 86686023HCID 86686023, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Conditions

Temperature
135 °C

Procedure

A reaction mixture of 4-bromo-6,7-dihydro-5H-isoquinolin-8-one (intermediate B-11 [C], 5.0 g, 22 mmol), 2,2-dimethyl-propane-1,3-diol (2.8 g, 26.5 mmol) and toluene-4-sulfonic acid (85 mg, 0.44 mmol) in toluene (100 mL) was heated at 135° C. for 12 hours. After cooling to room temperature, it was concentrated under reduced pressure to give a residue which was extracted between EtOAc and water. The organic layer was washed with brine, dried over anhy. Na2SO4, filtered, and concentrated in vacuo to give a crude product (6.1 g, 88.9%) as a light yellow solid. MS: 312.2 & 314.2 (M+H+).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationit was concentrated under reduced pressure
  3. customto give a residue which
  4. extractionwas extracted between EtOAc and water
  5. washThe organic layer was washed with brine
  6. customdried over anhy
  7. filtrationNa2SO4, filtered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d23a39dd15d946409b8d819fc2e88706
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

Loading…