Water → 8-Nitroquinoline-5-carbonitrile

HRID 513737Notes

Reaction equation

HRID 513737 reaction equation
C[CH2:2][N:3](C(C)C)C(C)C.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.Br[C:45]1[CH:54]=[CH:53][C:52]([N+:55]([O-:57])=[O:56])=[C:51]2[C:46]=1[CH:47]=[CH:48][CH:49]=[N:50]2.O>CN(C=O)C.[C-]#N.[C-]#N.[Zn+2]>[N+:55]([C:52]1[C:51]2[N:50]=[CH:49][CH:48]=[CH:47][C:46]=2[C:45]([C:2]#[N:3])=[CH:54][CH:53]=1)([O-:57])=[O:56]

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 5816185-Bromo-8-nitroquinolineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

Product 1

HCID 681834208-Nitroquinoline-5-carbonitrileYield 73.1%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Zn(CN)2 (739 mg, 6.3 mmol), DIPEA (0.41 ml, 2.37 mmol), X-phos (225 mg, 0.47 mmol) and Pd2 (dba)2 (90 mg, 0.16 mmol) were added to a degassed (with argon) solution of 5-bromo-8-nitroquinoline 470 (400 mg, 1.58 mmol) in DMF (4 ml) and the mixture was heated at 100° C. in microwave for 20 min. After cooling, the mixture was poured into water and the aqueous phase was extracted with EtOAc. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with n-hexane/EtOAc (96:4) as the eluent to give the title compound (230 mg, 63%).

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous phase was extracted with EtOAc
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by column chromatography with n-hexane/EtOAc (96:4) as the eluent

Sources & evidence

ORD record
ord-b6e36fbf44844ee79ce102d710ce0a09
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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