Hydrochloric Acid → 3-[Hydroxy(1-nitronaphthalen-2-yl)methyl]benzonitrile

HRID 1191302Notes

Reaction equation

HRID 1191302 reaction equation
CN(C)CCOCCN(C)C.C([Mg]Cl)(C)C.N#N.I[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[C:23]#[N:24].[N+:28]([C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][C:32]=1[CH:41]=[O:42])([O-:30])=[O:29].Cl>C1COCC1>[OH:42][CH:41]([C:32]1[CH:33]=[CH:34][C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:31]=1[N+:28]([O-:30])=[O:29])[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[C:23]#[N:24]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 18204Bis(dimethylaminoethyl) etherHCID 1443413-IodobenzonitrileHCID 45760221-Nitro-2-naphthaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 866904453-[Hydroxy(1-nitronaphthalen-2-yl)methyl]benzonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of bis(2-dimethylaminoethyl)ether (5.62 mL, 29.8 mmol) in THF (125 mL) was added a solution of 2M isopropylmagnesium chloride in THF (14.9 mL, 29.8 mmol) dropwise under N2 atmosphere at room temperature, and stirred for 20 min. To the mixture was added 3-iodobenzonitrile (5.69 g, 24.9 mmol), and stirred for 30 min. To an ice-cold solution of the resultant mixture was added 1-nitro-2-naphthaldehyde, and stirred at room temperature for 1 hour. To the reaction mixture was poured 1M hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1), to give the titled compound as a green orange oil (7.37 g, yield 97%).

Workup

  1. stirringstirred for 30 min
  2. stirringstirred at room temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-b20596e8c1404bb499e41b0d0a95b6f4
Source dataset
uspto-grants-2014_03
Patent number
US08680110B2

Reaction notes

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