Dimethylformamide → HCID 66596859, compound

HRID 1811413Notes

Reaction equation

HRID 1811413 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5](OS(C(F)(F)F)(=O)=O)=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[CH3:21][N:22](C=O)C>[C-]#N.[Zn+2].[C-]#N.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>[C:21]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:12])[NH:10]2)#[N:22]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 86613921HCID 86613921, compound

Product 1

HCID 66596859HCID 66596859, compoundYield 87%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

8-Methyl-5-trifluoromethanesulfonyloxy-3,4-dihydro-1H-quinolin-2-one (4.0 g), zinc cyanide (3.34 g) and tetrakis(triphenylphosphine)palladium (0.299 g) were suspended in DMF (40 ml), and the suspension was stirred at 100° C. for 4 hours. The insoluble matter was filtered off, and ethyl acetate was added to the filtrate, followed by washing with water. After drying over anhydrous magnesium sulfate, the dry product was concentrated, and the residue was recrystallized from a DMF-ethanol mixed solvent to thereby obtain 2.1 g (yield: 87%) of 5-cyano-8-methyl-3,4-dihydro-1H-quinolin-2-one as a light brown powder.

Workup

  1. filtrationThe insoluble matter was filtered off
  2. additionethyl acetate was added to the filtrate
  3. washby washing with water
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. concentrationthe dry product was concentrated
  6. customthe residue was recrystallized from a DMF-ethanol mixed solvent

Sources & evidence

ORD record
ord-d3121e490b874c439a616ddc3132bcb2
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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