1-Bromohexane → HCID 23084562, compound

HRID 2111629Notes

Reaction equation

HRID 2111629 reaction equation
N[C@H](C=O)CCSC.Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[CH3:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][C:25]=1[CH3:26])[C:22](=[O:27])[N:21]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)[C:20]2=[O:34].[NH4+].[Cl-]>O1CCCC1>[CH3:26][C:25]1[CH:24]=[C:23]2[C:19](=[CH:18][C:17]=1[CH3:16])[C:20](=[O:34])[N:21]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)[C:22]2([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[OH:27]

Participants

6

Reactant 4

HCID 81011-BromohexaneHCID 25517Ammonium ChlorideHCID 446793Methionin ALHCID 23084563HCID 23084563, compound

Product 1

HCID 23084562HCID 23084562, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Metal magnesium (0.14 g, 5.6 mmol) and 1-bromohexane (0.78 ml, 5.6 mmol) were stirred with heating at 65° C. in anhydrous tetrahydrofuran (24 ml) under an argon atmosphere for 2 hrs, and 5,6-dimethyl-2-(3-pyridyl)isoindolin-1,3-dione (0.40 g, 1.6 mmol) was added thereto, followed by stirring at 25° C. for 15 minutes. The reaction solution was poured into saturated aqueous NH4Cl solution, and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (chloroform:acetone=5:1) to give 0.23 g of 5,6-dimethyl-3-hexyl-3-hydroxy-2-(3-pyridyl)isoindolin-1-one.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (chloroform:acetone=5:1)

Sources & evidence

ORD record
ord-11b50b84898148818ef0e37339f3391b
Source dataset
uspto-grants-2009_04
Patent number
US07521451B2

Reaction notes

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