Acetonitrile → HCID 59496607, compound

HRID 449529Notes

Reaction equation

HRID 449529 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2.Br[CH2:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[C:24]#[N:25].C(#N)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C>[C:24]([C:23]1[CH:22]=[C:21]([CH:28]=[CH:27][CH:26]=1)[CH2:20][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)#[N:25]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 10538586tert-Butyl 5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 59496607HCID 59496607, compoundYield 109.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.025 g, 0.10 mmol) was combined with 3-(bromomethyl)benzonitrile (Aldrich, 145610) (0.029 g, 0.15 mmol), acetonitrile (2.0 mL) and cesium carbonate (0.065 g, 0.20 mmol) and was stirred at r.t. overnight. This was diluted with ethyl acetate, filtered to remove the solids and concentrated under reduced pressure to give crude tert-butyl 5-(3-cyanobenzyloxy)-3,4-dihydroisoquinoline-2(1H)-carboxylate (0.040 g) as a semisolid. Analytical LCMS (M+Na)+: m/z=387.0.

Workup

  1. filtrationfiltered
  2. customto remove the solids
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5c3f7cf940cc47f3bc97f9b6bd673ac2
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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