Dimethylformamide → 1-Oxo-2,3-Dihydro-1H-Indene-4-Carbonitrile

HRID 1187014Notes

Reaction equation

HRID 1187014 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].[CH3:12][N:13](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:11]=[C:6]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:2]([C:12]#[N:13])[C:3]=2[CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 987131-Indanone, 4-bromo-

Product 1

HCID 27515831-Oxo-2,3-Dihydro-1H-Indene-4-Carbonitrile

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
165 °C

Procedure

To a solution of 4-bromo-2,3-dihydro-1H-inden-1-one (1.00 g, 4.74 mmol) in 5 mL of DMF was added Zn(CN)2 (556 mg, 4.74 mmol) and Pd(PPh3)4 (77 mg, 0.14 mmol), and the reaction mixture was stirred under microwave irradiation for 1 h at 165° C. The solvent was removed in vacuum to afford the crude compound, which was purified via column chromatography to afford 1-oxo-2,3-dihydro-1H-indene-4-carbonitrile.

Workup

  1. customThe solvent was removed in vacuum
  2. customto afford the crude compound, which
  3. customwas purified via column chromatography

Sources & evidence

ORD record
ord-461d8197f16f48be9716d34c24515ec1
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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