4-Bromoanisole → HCID 13392804, compound

HRID 329964Notes

Reaction equation

HRID 329964 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](Br)=[CH:5][CH:4]=1.[CH2:10]([O:12][C:13]([C:15]1[N:16]=[CH:17][C:18]2[NH:19][C:20]3[C:25]([C:26]=2[C:27]=1[CH2:28][O:29][CH3:30])=[CH:24][C:23]([OH:31])=[CH:22][CH:21]=3)=[O:14])[CH3:11]>N1C(C)=CC(C)=CC=1C.[Cu-]=O>[CH2:10]([O:12][C:13]([C:15]1[N:16]=[CH:17][C:18]2[NH:19][C:20]3[C:25]([C:26]=2[C:27]=1[CH2:28][O:29][CH3:30])=[CH:24][C:23]([O:31][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[CH:22][CH:21]=3)=[O:14])[CH3:11]

Participants

5

Reactant 2

HCID 77304-BromoanisoleHCID 13392775HCID 13392775, compound

Product 1

HCID 13392804HCID 13392804, compoundYield 41.9%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 79532,4,6-TrimethylpyridineSolvent

Procedure

0.2 g of 4-methoxybromobenzene, 0.3 g of 6-hydroxy-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester, and 0.15 g of copper(I) oxide are heated in 5 ml of collidine to boiling for 35 hours. After cooling, the mixture is filtered and evaporated under vacuum. The residue is taken up in ethyl acetate, extracted repeatedly with ice-cold 25% ammonia solution and then washed with saturated sodium chloride solution, dried over calcium sulfate, and evaporated. Chromatography on silica gel with methylene chloride-ethanol (10:1) yields 0.17 g of 6-(4-methoxyphenoxy)-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester, mp 154.0° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered
  3. customevaporated under vacuum
  4. extractionextracted repeatedly with ice-cold 25% ammonia solution
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried over calcium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-6007a654add34519b85a692d6da68a34
Source dataset
uspto-grants-1990_01
Patent number
US04894377

Reaction notes

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