Dimethylformamide → HCID 57707881, compound

HRID 216868Notes

Reaction equation

HRID 216868 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([C:13]1[C:14]([CH3:19])=[N:15][CH:16]=[CH:17][CH:18]=1)[C:9]([CH:20](Cl)[CH3:21])=[CH:8]2.CN(C=O)C.[C:28]1(=[O:38])[NH:32][C:31](=[O:33])[C:30]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:29]12.[K]>>[Cl:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([C:13]1[C:14]([CH3:19])=[N:15][CH:16]=[CH:17][CH:18]=1)[C:9]([CH:20]([N:32]1[C:28](=[O:38])[C:29]3[C:30](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:31]1=[O:33])[CH3:21])=[CH:8]2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24194345Phthalimide potassium saltHCID 68942948HCID 68942948, compound

Product 1

HCID 57707881HCID 57707881, compound

Conditions

Temperature
100 °C

Procedure

To a stirring solution of 8-chloro-3-(1-chloroethyl)-2-(2-methylpyridin-3-yl)-quinoline hydrochloride (1.3130 g, 3.712 mmol) in DMF (18.56 m/L, 3.712 mmol) at 100° C. was added potassium phthalimide (1.719 g, 9.281 mmol) at 100° C. and the mixture was stirred at 100° C. After 1.5 h, the mixture was concentrated under reduced pressure and triturated with water (50 mL). The resulting solid was filtered and washed with 2 N NaOH (50 mL) and then with water (500 mL), and air-dried to give 2-(1-(8-chloro-2-(2-methylpyridin-3-yl)quinolin-3-yl)ethyl)-isoindoline-1,3-dione as a tan solid: LC-MS (ESI) m/z 428.0 [M+H]+. The impure product was carried on crude without purification for the next step.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customtriturated with water (50 mL)
  3. filtrationThe resulting solid was filtered
  4. washwashed with 2 N NaOH (50 mL)
  5. dry with materialwith water (500 mL), and air-dried

Sources & evidence

ORD record
ord-74e4058b719f4f138db05fdd4a362b85
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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