Dimethylcarbamoyl Chloride → 6-Phthalimidomethyl-2-pyridinecarbonitrile

HRID 499507Notes

Reaction equation

HRID 499507 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N+:8]1([O-])[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].C[Si]([C:24]#[N:25])(C)C.CN(C)C(Cl)=O>[N+](CC)([O-])=O.C(Cl)(Cl)Cl>[O:18]=[C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16](=[O:17])[N:8]1[CH2:7][C:2]1[N:1]=[C:6]([C:24]#[N:25])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 865964682-(2-Pyridylmethyl)-1H-isoindole-1,3(2H)-dione N-oxide

Product 1

HCID 100383916-Phthalimidomethyl-2-pyridinecarbonitrileYield 22.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6587NitroethaneSolvent

Conditions

Temperature
60 °C

Procedure

2-(2-Pyridylmethyl)-1H-isoindole-1,3(2H)-dione N-oxide (8.0 g, 31 mmol) was dissolved in mixed solvent of nitroethane (80 ml) and chloroform (150 ml), and trimethylsilyl cyanide (9.3 g, 94 mmol) and N,N-dimethylcarbamoyl chloride (6.8 g, 63 mmol) were added thereto. The mixture was stirred at room temperature for 4 hrs and at 60° C. for 24 hrs. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography. The fractions eluted with hexane-ethyl acetate (2:1, v/v) were collected, concentrated and recrystallized from hexane-tetrahydrofuran to give the titled compound (1.8 g, 22%) as white crystals.

Workup

  1. additionwere added
  2. customThe solvent was evaporated
  3. washThe fractions eluted with hexane-ethyl acetate (2:1
  4. customv/v) were collected
  5. concentrationconcentrated
  6. customrecrystallized from hexane-tetrahydrofuran

Sources & evidence

ORD record
ord-acd81c535e294316a0a2cd09c1a523c4
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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