Dimethylformamide → 2-Oxo-1,2,3,4-tetrahydroquinoline-7-carbonitrile

HRID 1256276Notes

Reaction equation

HRID 1256276 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:17])[NH:14]2)=[CH:9][CH:8]=1)(=O)=O.[CH3:20][N:21](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:17]=[C:13]1[CH2:12][CH2:11][C:10]2[C:15](=[CH:16][C:7]([C:20]#[N:21])=[CH:8][CH:9]=2)[NH:14]1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 594607892-Oxo-1,2,3,4-tetrahydroquinolin-7-yl trifluoromethanesulfonate

Product 1

HCID 586868452-Oxo-1,2,3,4-tetrahydroquinoline-7-carbonitrile

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst2×HCID 178418397HCID 178418397, compoundCatalyst2×

Conditions

Temperature
100 °C

Procedure

Step R1-2: The mixture of 2-oxo-1,2,3,4-tetrahydroquinolin-7-yl trifluoromethanesulfonate (338 g), Zn(CN)2 (134 g) and Pd(PPh3)4 (33.5 g) in DMF (3.0 L) was heated at 100° C. for 4 hours and cooled to room temperature. To the mixture, Zn(CN)2 (134 g) and Pd(PPh3)4 (12.7 g) were added and the mixture was stirred at 100° C. for 2 hours. After cooling to 60° C., the reaction mixture was filtrated through a pad of Celite. The filtrate was concentrated to obtain a solid. The solid was washed with EtOAc twice to obtain 2-oxo-1,2,3,4-tetrahydroquinoline-7-carbonitrile as a pale yellow solid (165 g).

Workup

  1. temperaturecooled to room temperature
  2. temperatureAfter cooling to 60° C.
  3. filtrationthe reaction mixture was filtrated through a pad of Celite
  4. concentrationThe filtrate was concentrated
  5. customto obtain a solid
  6. washThe solid was washed with EtOAc twice

Sources & evidence

ORD record
ord-e4b6188b907c43899b6dd4f462b0b7b6
Source dataset
uspto-grants-2013_06
Patent number
US08461182B2

Reaction notes

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