Water → 6-(6,7-Dimethoxyquinolin-4-yloxy)naphthalen-1-amine

HRID 1925272Notes

Reaction equation

HRID 1925272 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([OH:12])=[CH:7]2.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][CH:21]=1.O>CN1C(=O)CCC1.C(Cl)Cl>[CH3:31][O:30][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][C:26]=1[O:32][CH3:33])[N:23]=[CH:22][CH:21]=[C:20]2[O:12][C:6]1[CH:7]=[C:8]2[C:3](=[CH:4][CH:5]=1)[C:2]([NH2:1])=[CH:11][CH:10]=[CH:9]2

Participants

7

Reactant 4

HCID 962WaterHCID 68655-Amino-2-naphtholHCID 10796Cesium carbonateHCID 4596104-Chloro-6,7-dimethoxyquinoline

Product 1

HCID 675202746-(6,7-Dimethoxyquinolin-4-yloxy)naphthalen-1-amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 5-amino-2-naphthol (711 mg, 4.47 mmol) in NMP (3 ml), Cs2CO3 (4.37 g, 13.41 mmol) was added and the reaction was stirred at RT for 15 min. To the mixture, 4-chloro-6,7-dimethoxy-quinoline (500 mg, 2.23 mmol) was added and the vessel was sealed/clamped shut. The reaction was placed in the microwave and heated at 160° C. for 15 min, then 10 additional min with pre-stirring for 60 sec. The mixture was taken up into water and CH2Cl2, and filtered through Celite. The aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with water, 1N NaOH, and brine, dried with Na2SO4, filtered and concentrated in vacuo. The 6-(6,7-dimethoxy-quinolin-4-yloxy)-naphthalen-1-ylamine was purified by column chromatography using 0-10% MeOH in CH2Cl2.

Workup

  1. customthe vessel was sealed/clamped
  2. temperatureheated at 160° C. for 15 min
  3. stirring10 additional min with pre-stirring for 60 sec
  4. filtrationfiltered through Celite
  5. extractionThe aqueous layer was extracted with CH2Cl2
  6. washThe combined organic layers were washed with water, 1N NaOH, and brine
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe 6-(6,7-dimethoxy-quinolin-4-yloxy)-naphthalen-1-ylamine was purified by column chromatography

Sources & evidence

ORD record
ord-cc1bc29a5c0547ec93708c5fdcf61cc1
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

Loading…