1-Naphthylamine → N-(3-(1,3-dioxolan-2-yl)phenyl)naphthalen-1-amine

HRID 42395

反応式

HRID 42395 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.[C:13]1([NH2:23])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:4]1[CH:3]=[C:2]([NH:23][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)[CH:7]=[CH:6][CH:5]=1

参加物

7

反応物 4

HCID 86401-NaphthylamineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 873062-(3-Bromophenyl)-1,3-dioxolaneHCID 23676156Sodium t-butoxide

生成物 1

HCID 58028518N-(3-(1,3-dioxolan-2-yl)phenyl)naphthalen-1-amine

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

実験手順

A clean and dry 500 ml round bottom flask equipped with a reflux condenser, magnetic stir bar, and thermometer with adapter was prepared and purged with nitrogen Anhydrous toluene (250.0 ml) was transferred to this flask by cannula. 2-(3-bromophenyl)-1,3-dioxolane (6.0 ml, 0.0397 mol) was added by syringe followed by the manual addition of 1-naphthylamine (5.08 g, 0.0355 mol). The reaction solution was purged with a strong nitrogen flow for 30 minutes. Sodium tert-butoxide (5.60 g, 0.0583 mol) and Pd2dba3 (0.65 g, 0.0007 mol) were then added manually, followed by the addition of tri-tert-butylphosphine (1.30 g, 0.0064 mol) in toluene (˜10 ml) via syringe. The vessel was heated to reflux for approximately 5 hours. The reaction was then cooled to room temperature and filtered through a Celite and silica gel pad washing thoroughly with acetone and chloroform. Solvent was removed by rotary evaporation. The crude material was purified by flash column chromatography using ethyl acetate/hexane as an eluent. This provided pure product confirmed by NMR spectroscopy.

後処理

  1. customA clean and dry 500 ml round bottom flask
  2. customequipped with a reflux condenser, magnetic stir bar
  3. customthermometer with adapter was prepared
  4. custompurged with nitrogen Anhydrous toluene (250.0 ml)
  5. customwas transferred to this flask by cannula
  6. customThe reaction solution was purged with a strong nitrogen flow for 30 minutes
  7. temperatureThe vessel was heated
  8. temperatureto reflux for approximately 5 hours
  9. filtrationfiltered through a Celite and silica gel pad
  10. washwashing thoroughly with acetone and chloroform
  11. customSolvent was removed by rotary evaporation
  12. customThe crude material was purified by flash column chromatography

出典と根拠

ORDレコード
ord-e6054a3a14fb43a2bff01a7ca1b28c62
出典データセット
uspto-grants-2013_09
特許番号
US08535974B2

関連ノート

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