N-(4-Bromo-5,6,7,8-tetrahydronaphthalen-1-yl)-acetamide → N-(4-Cyano-5,6,7,8-tetrahydronaphthalen-1-yl)-acetamide

HRID 751030Notes

Reaction equation

HRID 751030 reaction equation
Br[C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([NH:12][C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=1.[C:16]([Cu])#[N:17]>CN(C=O)C>[C:16]([C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[C:5]([NH:12][C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=1)#[N:17]

Participants

4

Reactant 2

HCID 12710300N-(4-Bromo-5,6,7,8-tetrahydronaphthalen-1-yl)-acetamideHCID 178418546HCID 178418546, compound

Product 1

HCID 68460315N-(4-Cyano-5,6,7,8-tetrahydronaphthalen-1-yl)-acetamideYield 998.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of compound 2B (1 g, 3.7 mmol) and CuCN (0.335 g, 0.374 mmol) in anhydrous DMF (8 mL) was refluxed for 5 h. After cooling to rt, the reaction mixture was concentrated under reduced pressure to remove most of the DMF and the remaining residue triturated with EtOAc (5×). The combined EtOAc was washed with water and brine, dried (Na2SO4), and concentrated under reduced pressure to dryness to yield compound 2C (0.8 g) as a yellow solid.

Workup

  1. temperaturewas refluxed for 5 h
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customto remove most of the DMF
  4. customthe remaining residue triturated with EtOAc (5×)
  5. washThe combined EtOAc was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-81b9b1a22d9347d9828e57251081821b
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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