Potassium Carbonate → 3-(4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)benzonitrile

HRID 277876Notes

Reaction equation

HRID 277876 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].Br[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:23])[CH2:17][C:16]2([CH3:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>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.C1(C)C=CC=CC=1.O>[CH3:24][C:16]1([CH3:25])[C:15]2[C:20](=[CH:21][CH:22]=[C:13]([C:5]3[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=3)[C:1]#[N:2])[CH:14]=2)[NH:19][C:18](=[O:23])[CH2:17]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 107295896-bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 99653993-(4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)benzonitrile

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Prepared by coupling 3-cyanophenylboronic acid with an equivalent amount of 6-bromo-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one using a catalytic amount of tetrakis(triphenylphosphine)palladium(0) as a catalyst with overnight refluxing in toluene containing an equivalent amount of potassium carbonate dissolved in water in the usual manner followed by recrystallization from ethanol gave a gray solid: mp. 190-192° C.; 1H-NMR (DMSO-d6) δ 10.29 (s, 1H), 8.17 (s, 1H), 8.00 (d, 1H, J=7.9 Hz), 7.77 (d, 1H, J=6.4 Hz), 7.65 (m, 2H), 7.55 (d, 1H, J=8.2 Hz), 6.97 (d, 1H, J=8.3 Hz), 2.40 (s, 2H), 1.30 (s, 6H); MS (APCI(−)) m/z 275 [M−H]− Anal. Calc. For C18H16N2O 0.25H2O: C, 75.77, H, 6.01, N, 9.82. Found: C, 75.45, H, 5.65, N, 920.

Workup

  1. customPrepared
  2. customwith overnight
  3. customfollowed by recrystallization from ethanol
  4. customgave a gray solid

Sources & evidence

ORD record
ord-da70df2f277a458ba7910cb44b6b10dd
Source dataset
uspto-grants-2002_03
Patent number
US06358948B1

Reaction notes

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