Methanol → 5-Methoxy-7-(3,4,5-trimethoxyphenyl)quinoline

HRID 1496865Notes

Reaction equation

HRID 1496865 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:14]=[C:15]([OH:23])[C:16]3[CH:17]=[CH:18][CH:19]=[N:20][C:21]=3[CH:22]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].CO.[C:26]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1>C(Cl)Cl>[CH3:26][O:23][C:15]1[CH:14]=[C:13]([C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]2

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 1364132517-(3,4,5-Trimethoxyphenyl)quinolin-5-ol

Product 1

HCID 712382355-Methoxy-7-(3,4,5-trimethoxyphenyl)quinolineYield 11.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

100 mg of 7-(3,4,5-Trimethoxyphenyl)quinolin-5-ol, 42 μL of MeOH and 480 mg of triphenylphosphine was dissolved in 5 mL of DCM. 435 mg of DBAD was added and the mixture stirred for 3 days at room temperature. The mixture was diluted with DCM and extracted with 1N NaOH and water. The organic phase was concentrated in vacuo and purified with HPLC (XbridgeC18, MeOH/water, TFA) to yield after lyophilisation 12 mg of Example 3 as solid.

Workup

  1. extractionextracted with 1N NaOH and water
  2. concentrationThe organic phase was concentrated in vacuo
  3. custompurified with HPLC (XbridgeC18, MeOH/water, TFA)

Sources & evidence

ORD record
ord-8511d91f21ea43d9b642a8920f4234b1
Source dataset
uspto-grants-2015_12
Patent number
US09199937B2

Reaction notes

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