HCID 86718154, compound → HCID 86718155, compound

HRID 2205172Notes

Reaction equation

HRID 2205172 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[N:5]=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:3]=1[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1>[Pd].C(O)(=O)C>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([C:4]2[C:3]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[CH:2][C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=3)[N:5]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 86718154HCID 86718154, compound

Product 1

HCID 86718155HCID 86718155, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of ethyl 4-chloro-2,3-bis(4-methoxyphenyl)quinoline-6-carboxylate (150 mg, 0.33 mmol, 1.00 equiv), acetic acid (10 mL), NH4OAc (102 mg, 1.67 mmol, 5.00 equiv), and palladium on carbon (150 mg) were placed in a 25-mL round-bottom flask and stirred overnight at 40° C. in an oil bath under an atmosphere of H2(g). The resulting mixture was concentrated, then diluted with 30 ml of ethyl acetate and washed with 10 ml of NaHCO3 (aq.). The organic layer was concentrated in vacuo and purified via silica gel chromatography (PE:EA=30:1) affording 100 mg of ethyl 2,3-bis(4-methoxyphenyl)quinoline-6-carboxylate as yellow solid.

Workup

  1. customwere placed in a 25-mL round-bottom flask
  2. concentrationThe resulting mixture was concentrated
  3. additiondiluted with 30 ml of ethyl acetate
  4. washwashed with 10 ml of NaHCO3 (aq.)
  5. concentrationThe organic layer was concentrated in vacuo
  6. custompurified via silica gel chromatography (PE:EA=30:1)

Sources & evidence

ORD record
ord-6817daebb6594541b2cc8c6f0bd08b96
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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