N-3-Bromopropylphthalimide → 5-(4-Phthalimidopropyloxyphenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile

HRID 728904Notes

Reaction equation

HRID 728904 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:16]#[N:17])[C:11](=[O:15])[NH:12][C:13]=2[CH3:14])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Br[CH2:23][CH2:24][CH2:25][N:26]1[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36]>CN(C=O)C>[C:27]1(=[O:36])[N:26]([CH2:25][CH2:24][CH2:23][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:9]=[C:10]([C:16]#[N:17])[C:11](=[O:15])[NH:12][C:13]=3[CH3:14])=[CH:6][CH:7]=2)[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]12

Participants

6

Reactant 4

HCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 133747555-(4-Hydroxyphenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 543645795-(4-Phthalimidopropyloxyphenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrileYield 51.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
80 °C

Procedure

A solution of 2.00 g (8.84 mmol) of 5-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile in 15 ml of DMF is added dropwise to a suspension of 707 mg (17.7 mmol) of 60% sodium hydride-mineral oil in DMF (5 ml). When hydrogen evolution ceases, the mixture is warmed to 60° C. and a solution of 2.37 g (8.84 mmol) of N-(3-bromopropyl)phthalimide in 5 ml of DMF is added dropwise. After 1 hr at 60° C., the temperature of the mixture is raised to 80° C. for an additional hr of heating. After cooling, the DMF is removed under vacuum. The residue is triturated with water and EtOAc to give a yellow solid that is collected by suction filtration. Thissolid is dried at 80° C. under vacuum to give 1.885 g of 5-(4-phthalimidopropyloxyphenyl)-6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile as a yellow solid. 1H-NMR (d6 -DMSO): δ 2.07 (t,2H); 2.23 (s,3H); 3.78 (t,2H); 4.05 (t,2H); 6.83 (d, 2H); 7.20 (d,2H): 7.80 (m, 4H); 8.00 (s, 1H).

Workup

  1. temperatureof heating
  2. temperatureAfter cooling
  3. customthe DMF is removed under vacuum
  4. customThe residue is triturated with water and EtOAc
  5. customto give a yellow solid
  6. filtrationthat is collected by suction filtration
  7. customThissolid is dried at 80° C. under vacuum

Sources & evidence

ORD record
ord-7dd52160e0d04112a3b1ab86b7433328
Source dataset
uspto-grants-1991_09
Patent number
US05051431

Reaction notes

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