Acetic Acid → HCID 23511438, compound

HRID 353783Notes

Reaction equation

HRID 353783 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16].[N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[CH:27]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[CH3:2][N:3]([CH2:27][C:18]1[CH:19]=[CH:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:17]=1)[CH2:4][CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 796192-QuinolinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23511414HCID 23511414, compound

Product 1

HCID 23511438HCID 23511438, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the HCl salt of 2-(2-Methylamino-ethyl)-isoindole-1,3-dione (1 eq) in dichloromethane was added quinoline-2-carbaldehyde(1.2 eq), sodium triacetoxyborohydride (2 eq), and acetic acid (1.2 eq) at rt.; the solution was allowed to stir for 16 hours. After concentration, the solution was diluted with ethyl acetate, washed with NaHCO3(sat), NaCl(sat), dried over MgSO4, filtered, concentrated and pumped on. The yellow oil was then purified using flash chromatography (2% methanol/dichloromethane with 0.1% triethylamine) to yield 2-[2-(Methyl-quinolin-2-ylmethyl-amino)-ethyl]-isoindole-1,3-dione as a green solid. MH+(346).

Workup

  1. concentrationAfter concentration
  2. additionthe solution was diluted with ethyl acetate
  3. washwashed with NaHCO3(sat), NaCl(sat)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe yellow oil was then purified

Sources & evidence

ORD record
ord-58125a585e604678bee1c0ef2d6c9ca4
Source dataset
uspto-grants-2004_06
Patent number
US06756359B2

Reaction notes

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