Ethanol → HCID 57707852, compound

HRID 1397784Notes

Reaction equation

HRID 1397784 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:19][N:20]2C(=O)C3C(=CC=CC=3)C2=O)=[N:10][C:11]2[C:16]([N:17]=1)=[C:15]([I:18])[CH:14]=[CH:13][CH:12]=2.C(O)C.NN>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH2:19][NH2:20])=[N:10][C:11]2[C:16]([N:17]=1)=[C:15]([I:18])[CH:14]=[CH:13][CH:12]=2

Participants

4

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 57707784HCID 57707784, compound

Product 1

HCID 57707852HCID 57707852, compound

Procedure

To a suspension of 2-((3-(2-chlorophenyl)-5-iodoquinoxalin-2-yl)methyl)-isoindoline-1,3-dione (0.7028 g, 1.337 mmol) in ethanol (12.00 mL, 1.337 mmol) was added hydrazine, anhydrous (0.4196 mL, 13.37 mmol), and the mixture was stirred under reflux. After 30 min, the mixture was cooled to room temperature. The mixture was concentrated under reduced pressure. The residue was purified by column chromatography on a 80 g of Redi-Sep™ column using 0% to 50% gradient of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 over 25 min, and then 50% isocratic of CH2Cl2:MeOH:NR4OH (89:9:1) in CH2Cl2 for 5 min as eluent to give (3-(2-chlorophenyl)-5-iodoquinoxalin-2-yl)methanamine as a green syrupy solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.45 (1 H, dd, J=7.4, 1.0 Hz), 8.17 (1 H, dd, J=8.4, 1.2 Hz), 7.52-7.74 (5 H, m), 3.83 (2 H, br. s.), 1.97 (2 H, br. s.); LC-MS (ESI) m/z 396.0 [M+H]+.

Workup

  1. temperatureunder reflux
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on a 80 g of Redi-Sep™ column
  4. customover 25 min

Sources & evidence

ORD record
ord-84b42505d49c4b259d57283e02f901bd
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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