Methanol → HCID 86749665, compound

HRID 1736411Notes

Reaction equation

HRID 1736411 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([CH2:13][NH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:20]=[N:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)[O:10]2)=[CH:5][CH:4]=1.[OH-].[Na+].CO>Br.C(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([CH2:13][NH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:20]=[N:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)[O:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86749664HCID 86749664, compound

Product 1

HCID 86749665HCID 86749665, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 7-{3-[(7-methoxy-chroman-2-ylmethyl-amino]-propanoxy}-quinoline (2.19 g, 5.7 mmol) in 48% aqueous HBr was heated to reflux for 3 hours. The reaction mixture was then allowed to cool to room temperature and basified with 1N sodium hydroxide until pH 12. The basic reaction mixture was extracted with ethyl acetate (2×100 mL), dried over anhydrous magnesium sulfate, filtered, and the solvent removed under vacuum. Chromatography (7% methanol in methylene chloride containing 1% ammonium hydroxide) afforded 1.34 g of the title compound (63% yield). The corresponding oxalate salt was prepared by adding an excess of oxalic acid in warm ethanol to a solution of the free base in warm ethanol; mp 195.5°-196.5° C.

Workup

  1. temperatureto reflux for 3 hours
  2. customThe basic reaction mixture
  3. extractionwas extracted with ethyl acetate (2×100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-721fc8e1f2ee447a81e6685856e710ec
Source dataset
uspto-grants-1996_07
Patent number
US05541199

Reaction notes

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