Ethanol → HCID 68533639, compound

HRID 2389362Notes

Reaction equation

HRID 2389362 reaction equation
[C:1]1([CH:7]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:27])[N:12]([CH2:14][CH2:15][N:16]3C(=O)C4C(=CC=CC=4)C3=O)[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCO.O.NN>C1COCC1>[NH2:16][CH2:15][CH2:14][N:12]1[CH:13]=[C:8]([CH:7]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:9]=[CH:10][C:11]1=[O:27]

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 68533592HCID 68533592, compound

Product 1

HCID 68533639HCID 68533639, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{2-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]ethyl}-1H-isoindole-1,3(2H)-dione (295 mg) in mixed solvent (EtOH:THF=4.4 mL:2.2 mL) was added hydrazine hydrate (329 μL) and the mixture was stirred at ambient temperature for 1 hour. The resulting mixture was evaporated in vacuo and the residue was diluted with chloroform (10 mL). The mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:MeOH=99:1-96:4) to afford 1-(2-aminoethyl)-5-(diphenylmethyl)-2(1H)-pyridinone (154 mg) as colorless crystals.

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. additionthe residue was diluted with chloroform (10 mL)
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (chloroform:MeOH=99:1-96:4)

Sources & evidence

ORD record
ord-0fdd8f256ebd445194a2443b885e3da5
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

Loading…