Ethanol → (8-Benzyloxy-quinolin-2-yl)[4-(2-methoxy-ethoxy)-2-nitro-phenyl]-amine

HRID 1745910Notes

Reaction equation

HRID 1745910 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16](Cl)[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1(C)C=CC=C[CH:21]=1.COCCO[C:32]1C=C[C:35]([N+:39]([O-:41])=[O:40])=[C:36]([NH2:38])[CH:37]=1.[C:42]([O-:45])([O-])=O.[Cs+].[Cs+].[CH3:48][CH2:49][OH:50]>ClCCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(B(O)O)C=CC=CC=1.C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([NH:38][C:36]1[CH:37]=[CH:32][C:49]([O:50][CH2:20][CH2:21][O:45][CH3:42])=[CH:48][C:35]=1[N+:39]([O-:41])=[O:40])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

10

Reactant 5

HCID 702EthanolHCID 1140TolueneHCID 10796Cesium carbonateHCID 220422348-(Benzyloxy)-2-chloroquinolineHCID 222269815-(2-Methoxyethoxy)-2-nitroaniline

Product 1

HCID 22226911(8-Benzyloxy-quinolin-2-yl)[4-(2-methoxy-ethoxy)-2-nitro-phenyl]-amine

Reagents, catalysts & solvents 4

HCID 66827Phenylboronic AcidCatalystHCID 742671,2-Bis(diphenylphosphino)ethaneCatalystHCID 167845palladium(II) acetateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
95 °C

Procedure

8-Benzyloxy-2-chloro-quinoline 77B (25.53 g, 94.64 mMol) was added to 350 mL of anhydrous toluene under an atmosphere of dry N2. To this solution was added 5-(2-methoxyethoxy)-2-nitro-phenylamine 42A (20.08 g, 94.64 mMol), palladium acetate (433 mg, 1.89 mMol), Cs2CO3 (43.2 g, 132 mMol), phenyl boronic acid (584 mg, 4.79 mMol) and 1,2-bis(diphenylphosphino)-ethane (2.33 g, 5.68 mMol) and the mixture was then deoxygenated by bubbling argon through for ten minutes. The reaction mixture was then heated to 95° C. and reacted at this temperature for two hours. Then the reaction was diluted (while still hot) with 350 mL of DCE and then filtered while still hot. The filter cake was washed with 100 mL of hot DCE. The filtrate was concentrated to ˜175 mL during which time a large amount of precipitate formed. To this mixture was added 400 mL of EtOH and the reaction mixture was stirred overnight. The resulting red precipitate was collected via suction filtration and dried under vacuum to give 36.8 g of the title compound as a red solid 77C.

Workup

  1. customthe mixture was then deoxygenated
  2. customby bubbling argon through for ten minutes
  3. customreacted at this temperature for two hours
  4. filtrationfiltered while still hot
  5. washThe filter cake was washed with 100 mL of hot DCE
  6. concentrationThe filtrate was concentrated to ˜175 mL during which time a large amount of precipitate
  7. customformed
  8. filtrationThe resulting red precipitate was collected via suction filtration
  9. customdried under vacuum

Sources & evidence

ORD record
ord-7e09eb6d1d134423a3da7ca4b81d8058
Source dataset
uspto-grants-2006_03
Patent number
US07019147B1

Reaction notes

Loading…