HCID 16069467, compound → 5-Chloronaphthalene-2-carbonitrile

HRID 1629720Notes

Reaction equation

HRID 1629720 reaction equation
ClC(Cl)(Cl)C(O[C:6]1[CH:11]=C[C:9](C#N)=[CH:8][C:7]=1CC=C)=O.[Cl-:19].N1C=CC=CC=1CN1C=C[N+]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=C1>ClCCCl.Cl[Cu]>[Cl:19][C:6]1[CH:11]=[CH:32][CH:33]=[C:38]2[C:7]=1[CH:8]=[CH:9][C:36]([C:35]#[N:34])=[CH:37]2

Participants

5

Reactant 2

HCID 16069467HCID 16069467, compoundHCID 57517331HCID 57517331, compound

Product 1

HCID 125518775-Chloronaphthalene-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A solution of INT 26 (1.01 g, 3.6 mmol) in degassed 1,2-dichloroethane (20 mL) containing CuCl (14.3 mg, 0.144 mmol) and 1,3-bis(pyridin-2-ylmethyl)-1H-imidazol-3-ium chloride (41.3 mg, 0.144 mmol, prepared according to: Journal of Organometallic Chemistry (2001), Vol. 617-618, 546-560.) was irradiated in the microwave for 2 hours at 200° C. and concentrated. The residue was purified by flash chromatography on silica gel (cyclohexane/EtOAc) to give INT 27.

Workup

  1. customwas irradiated in the microwave for 2 hours at 200° C.
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography on silica gel (cyclohexane/EtOAc)
  4. customto give INT 27

Sources & evidence

ORD record
ord-6958c70fe42f4eb1bce963ffec09a4b4
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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