Potassium Carbonate → HCID 67520335, compound

HRID 1925255Notes

Reaction equation

HRID 1925255 reaction equation
C(OC(=O)[NH:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([OH:22])[C:17]=2[CH3:21])[CH:12]=1)C1C=CC=CC=1.Cl[C:25]1[C:34]2[C:29](=[CH:30][C:31]([O:37][CH3:38])=[C:32]([O:35][CH3:36])[CH:33]=2)[N:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.[OH-].[Na+].[Cu]>[CH3:36][O:35][C:32]1[CH:33]=[C:34]2[C:29](=[CH:30][C:31]=1[O:37][CH3:38])[N:28]=[CH:27][CH:26]=[C:25]2[O:22][C:16]1[C:17]([CH3:21])=[C:18]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([NH2:10])[CH:20]=[CH:19]2

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 67520233HCID 67520233, compound

Product 1

HCID 67520335HCID 67520335, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

(6-Hydroxy-5-methyl-naphthalen-2-yl)-carbamic acid benzyl ester (Step a, 0.300 g, 0.9 mmol), 4-chloro-6,7-dimethoxy-quinoline (0.218 g, 0.9 mmol), K2CO3 (0.124 g, 0.9 mmol), and copper (4% by wt.) were added to a vial, then microwaved for 30 min at 120° C. with 150 watts of power (Powermax, CEM). The mixture was diluted with CH2Cl2 and 40 mL of 1N NaOH, then extracted the organics 3 times with CH2Cl2. The organics were combined, dried over Na2SO4, filtered, and concentrated in vacuo. The crude was crystallized from CH2Cl2/Hexanes to give a light brown solid, which was the titled compound. MS (ESI, pos. ion) m/z: 361 (M+1). Mass Calc'd for C22H20N2O3: 360.15.

Workup

  1. customthen microwaved for 30 min at 120° C. with 150 watts of power (Powermax, CEM)
  2. extractionextracted the organics 3 times with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude was crystallized from CH2Cl2/Hexanes
  7. customto give a light brown solid, which

Sources & evidence

ORD record
ord-487f51b8378d4fbb999e8121d7314ac0
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

Loading…