Dimethylformamide → 5-Oxo-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

HRID 719165Notes

Reaction equation

HRID 719165 reaction equation
Br[C:2]1[C:7]2=[CH:8][CH:9]=[C:10]3[C:19](N=C4C(C=CC=C4C(O)=O)=N3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[Cu][C:24]#[N:25].CN(C)C=[O:29]>O>[C:24]([C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:7]=1[CH2:8][CH2:9][CH2:10][C:19]2=[O:29])#[N:25]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 110786974-Bromo-benzo[a]phenazine-11-carboxylic AcidHCID 178418546HCID 178418546, compound

Product 1

HCID 109318735-Oxo-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromotetralone (see Reference Example 1C)(5.0 g) in N,N-dimethylformamide (20 mL) was added copper (1) cyanide (6.39 g) and the reaction mixture heated to reflux for 20 hours. The reaction mixture was then cooled to 80° C. and a solution of FeCl3.6H2O (24 g) in water (38 mL) was added. After stirring for a further 45 minutes the reaction mixture was cooled, diluted with water, extracted into toluene, washed with water, dried (MgSO4) and the solvent removed in vacuo to yield 5-cyano-1-tetralone as a yellow solid.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 20 hours
  3. temperaturewas cooled
  4. extractionextracted into toluene
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1de59b5afcca43669632f351b186fe0f
Source dataset
uspto-grants-2006_11
Patent number
US07132419B2

Reaction notes

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