Water → 2,2-dimethyl-7-(2-dimethylaminoethoxy)-4(6-methoxy-2-naphthyl)-2H-chromene

HRID 26298

Reaction equation

HRID 26298 reaction equation
[CH3:1][C:2]1([CH3:25])[CH:11]=[C:10]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([OH:24])=[CH:7][CH:8]=2)[O:3]1.[H-].[Na+].[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31]Cl.O>C1(C)C=CC=CC=1.CCOCC>[CH3:1][C:2]1([CH3:25])[CH:11]=[C:10]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=3)[CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([O:24][CH2:31][CH2:30][N:29]([CH3:33])[CH3:28])=[CH:7][CH:8]=2)[O:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 205704934-(6-Methoxynaphthalen-2-yl)-2,2-dimethyl-2H-1-benzopyran-7-ol

Product 1

HCID 205705022,2-dimethyl-7-(2-dimethylaminoethoxy)-4(6-methoxy-2-naphthyl)-2H-chromene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a refluxing solution of 2,2-dimethyl-7-hydroxy-4(6-methoxy-2-naphthyl)-2H-chromene (6.4 g, 0.019 mole) and sodium hydride (1.4 g, 80% dispersion in oil) in toluene (150 ml) was added dropwise 2-dimethylaminoethyl chloride (2.7 g, 0.025 mole). After refluxing for 3 hours the solution was cooled and water added. The organic layer was separated and removal of the solvent gave a residue which dissolved in ether and extracted with dilute hydrochloric acid (3×). The combined acid extracts were basified with 40% sodium hydroxide solution and extracted with ether (3×). The combined ether extracts were dried and removal of the solvent gave a quantitative yield of 2,2-dimethyl-7-(2-dimethylaminoethoxy)-4(6-methoxy-2-naphthyl)-2H-chromene which was converted to the hydrochloride salt m.p. 96°-98° C.

Workup

  1. temperatureAfter refluxing for 3 hours the solution
  2. temperaturewas cooled
  3. customThe organic layer was separated
  4. customremoval of the solvent
  5. customgave a residue which
  6. extractionextracted with dilute hydrochloric acid (3×)
  7. extractionextracted with ether (3×)
  8. dry with materialThe combined ether extracts were dried
  9. customremoval of the solvent

Sources & evidence

ORD record
ord-042c705f2590490aa966fada0c6c7821
Source dataset
uspto-grants-1979_04
Patent number
US04148909

Linked notes

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