Pyridine → N-Methoxy-N-methyl-5,6-dimethoxy-3-phenyl-1,2,3,4-tetrahydro-naphthalene-1-carboxamide

HRID 233407ノート

反応式

HRID 233407 の反応式
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH:6]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:7][CH:8]2[C:15](O)=[O:16].C(Cl)(=O)C(Cl)=O.Cl.[CH3:31][NH:32][O:33][CH3:34].N1C=CC=CC=1>C1(C)C=CC=CC=1.C(O)C>[CH3:34][O:33][N:32]([CH3:31])[C:15]([CH:8]1[C:9]2[C:4](=[C:3]([O:2][CH3:1])[C:12]([O:13][CH3:14])=[CH:11][CH:10]=2)[CH2:5][CH:6]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:7]1)=[O:16]

参加物

7

反応物 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 199611505,6-Dimethoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid

生成物 1

HCID 19961165N-Methoxy-N-methyl-5,6-dimethoxy-3-phenyl-1,2,3,4-tetrahydro-naphthalene-1-carboxamide収率 98%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

5,6-Dimethoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (5 g, 16 mmol), from Step 3, was suspended in 100 mL of toluene and 5 mL of oxalyl chloride was added. The reaction mixture was heated at reflux temperature for 1.5 h under a nitrogen atmosphere. The solvent was evaporated and excess reagents removed from the residue as an azeotrope with toluene (2×40 mL). The acid chloride and 2g (20 mmol) of N,O-dimethylhydroxylamine hydrochloride was dissolved in 80 mL of ethanol-free chloroform. The solution was cooled to 0° C. and 3.3 mL of pyridine was added slowly. The reaction mixture was allowed to warm to ambient temperature and stirred at ambient temperature for approximately 4 h then evaporated to dryness. The residue was dissolved in a 1:1 mixture of diethyl ether and methylene chloride and washed with brine. The layers were separated and the organic layer dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound as an oil in 98% yield. The product of Step 4 was used in the next step without purification.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 1.5 h under a nitrogen atmosphere
  3. customThe solvent was evaporated
  4. customexcess reagents removed from the residue as an azeotrope with toluene (2×40 mL)
  5. temperatureto warm to ambient temperature
  6. customthen evaporated to dryness
  7. dissolutionThe residue was dissolved in a 1:1 mixture of diethyl ether and methylene chloride
  8. washwashed with brine
  9. customThe layers were separated
  10. dry with materialthe organic layer dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-674ba99cc63d4804b4171f0b579cb3f6
出典データセット
uspto-grants-1997_01
特許番号
US05591884

反応ノート

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