1,3-Propanediol → HCID 67061859, compound

HRID 1892025Notes

Reaction equation

HRID 1892025 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:22])[N:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:8](=[O:15])[C:9]3[C:14]=2[C:13]=1[CH:12]=[CH:11][CH:10]=3.[OH-].[Na+].[CH2:25]([OH:29])[CH2:26][CH2:27][OH:28]>O>[OH:28][CH2:27][CH2:26][CH2:25][O:29][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:22])[N:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:8](=[O:15])[C:9]3[C:14]=2[C:13]=1[CH:12]=[CH:11][CH:10]=3

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 14798Sodium HydroxideHCID 1547824HCID 1547824, compound

Product 1

HCID 67061859HCID 67061859, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-bromo-2-phenyl-benzo[de]isoquinoline-1,3-dione (4.0 g), sodium hydroxide (0.67 g) and 1,3-propane diol (50 ml) was maintained with stirring at 120° C. for 10 hrs. The reaction mixture was cooled to room temperature. Water (100 ml) was added to the mixture and solid separated out. The solid was filtered, washed with water, and dried at 100° C. for 8 hours to provide a crude product in a yield of 1.90 g. The crude product was purified using mono chloro benzene (60 ml) and activated charcoal (0.20 g). The weight of the of the purified product obtained was 1.15 g. 1H-NMR: 3.93 δ (m, 2 protons); 4.35 δ (m, 1 proton); 2.25 δ (m, 2 protons); 3.96 δ (m, 2 protons); 4.47 δ (m, 2 proton); 7.13 δ (m, 2 protons); 5.14 δ (m, 1 proton); 7.36 δ (m, 3 protons); 7.51 δ (m, 3 protons); 7.84 δ (m, 1 proton); 8.46 δ (m, 2 protons); 8.69 δ (m, 1 proton).

Workup

  1. temperaturewas maintained
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customseparated out
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customdried at 100° C. for 8 hours

Sources & evidence

ORD record
ord-651440f3c35b4357b7652f3664d44e6d
Source dataset
uspto-grants-2013_08
Patent number
US08507590B2

Reaction notes

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