Water → HCID 178487709, compound

HRID 925960Notes

Reaction equation

HRID 925960 reaction equation
[CH:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([CH3:3])[CH3:2].Cl[C:10]1[CH:19]=[C:18]([O:20]CC2C=CC(OC)=CC=2)[C:17]2[C:12](=[C:13]([CH3:32])[C:14]([O:30][CH3:31])=[CH:15][CH:16]=2)[N:11]=1.O>CN1CCCC1=O>[OH:20][C:18]1[C:17]2[C:12](=[C:13]([CH3:32])[C:14]([O:30][CH3:31])=[CH:15][CH:16]=2)[N:11]=[C:10]([N:6]2[CH:7]=[CH:8][C:4]([CH:1]([CH3:3])[CH3:2])=[N:5]2)[CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 566051592-Chloro-8-methyl-7-methoxy-4-(4-methoxy-benzyloxy)-quinolineHCID 178439403HCID 178439403, compound

Product 1

HCID 178487709HCID 178487709, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of compound 233b (350 mg, 1 eq.) and compound 221b (480 mg, 6 eq.) in N-methylpyrrolidone (5 mL) was heated at 200° C. for 30 min. After the reaction mixture was cooled to room temperature, water was added. The mixture was extracted with EtOAc, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel (EtOAc/DCM). Recrystallisation in diethylether gave compound 236b as a white solid in 49% yield. 1H NMR (CDCl3, 376 MHz) δ (ppm) 1.35 (s, 3H), 1.36 (s, 3H), 2.85 (s, 3H), 3.97 (s, 3H), 6.40 (d, J=2.65 Hz, 2H), 7.01 (d, J=9.00 Hz, 1H), 8.00 (brs, 1H), 8.23 (d, J=9.00 Hz, 1H), 9.81 (brs, 1H); MS (ESI, EI+): m/z=298 (MH+).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by chromatography on silica gel (EtOAc/DCM)
  6. customRecrystallisation in diethylether

Sources & evidence

ORD record
ord-bb816fbaf90d4806b35c6c989c72f9e9
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

Loading…