HCID 58036788, compound → HCID 58036799, compound

HRID 1952007Notes

Reaction equation

HRID 1952007 reaction equation
[C:1]1([P:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[NH:17][CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]=[CH:14]3)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCOC(C)=O.[Pd]>[C:25]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[C:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:15]=[CH:14]3)=[O:8])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 1

HCID 58036788HCID 58036788, compound

Product 1

HCID 58036799HCID 58036799, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 8-diphenylphosphinoyl-2-phenyl-1,2-dihydroquinoline (8) (1.2 g, 2.95 mmol) in EtOAc (40 mL) was added Pd/C (1.2 g, 100 wt %) and the suspension was stirred overnight at room temperature. The mixture was then filtered over celite and evaporated to give 9 (1.19 g) quantitatively as a white solid. 1H NMR (400.13 MHz, CDCl3) δ 8.63 (dd, 1H, J=14.0, 7.2 Hz, C7—H), 8.16 (dd, 1H, J=8.8, 1.2 Hz, C5—H), 7.86 (1H, d, J=8.4 Hz, C3—H), 7.91 (dd, 4H, J=12.4, 7.2 Hz, Ph-H), 7.81 (dd, 1H, J=8.4 Hz, C4—H), 7.65 (td, 1H, J=8.0, 2.0 Hz, C6—H), 7.5-7.2 (m, 11H, Ph-H) ppm; 13C NMR (100.61 MHz, CDCl3) δ 156.2, 147.4 (d, J=6.1 Hz), 138.4, 137.7 (d, J=7.1 Hz), 136.8, 134.3, 133.2, 132.2, 132.1, 131.9, 131.0, 129.3, 128.3, 128.0, 127.8, 127.4, 125.9, 125.7, 118.7 ppm; 31P NMR (161.97 MHz, CDCl3) δ 27.7 ppm.

Workup

  1. filtrationThe mixture was then filtered over celite
  2. customevaporated

Sources & evidence

ORD record
ord-5fcbb62d642645738bf78a9c4375c35c
Source dataset
uspto-grants-2013_03
Patent number
US08404843B2

Reaction notes

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