Hydrochloric Acid → 2-(4-Methoxy-3-methylphenyl)ethan-1-amine

HRID 2251492

反応式

HRID 2251492 の反応式
[CH3:1][C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[N+:10]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:13][CH3:14].B.Cl>C1COCC1>[CH3:14][O:13][C:3]1[CH:4]=[CH:5][C:6]([CH2:8][CH2:9][NH2:10])=[CH:7][C:2]=1[CH3:1]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 9584691-Methoxy-2-methyl-4-(2-nitroethenyl)benzene

生成物 1

HCID 64846602-(4-Methoxy-3-methylphenyl)ethan-1-amine収率 81%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of methyl 2-methyl-4-[(E)-2-nitroethenyl]phenyl ether (7.89 g; 40.88 mmol) in dry THF (50 ml) was added to borane (245 ml of 1M solution in THF; 245 mmol), under nitrogen, dropwise over 20 minutes. The reaction mixture was then heated to 90C. After 14 hr it was cooled to rt and ice-cold water (100 ml) was added dropwise over 30 minutes. The pH was adjusted to ˜2 with 1N HCl and heated to reflux for 5 hr. Upon cooling, the reaction mixture was extracted with ethyl ether (2×300 ml) and the ether phases were discarded. The pH of the aqueous phase was adjusted to 10 with 1N NaOH and extracted with ethyl ether (2×200 ml). The combined organic phases were dried over MgSO4, filtered and concentrated to provide 2-(4-methoxy-3-methylphenyl)ethanamine (5.46 g; 81% yield), which was used without any further purification.

後処理

  1. temperatureheated
  2. temperatureto reflux for 5 hr
  3. temperatureUpon cooling
  4. extractionthe reaction mixture was extracted with ethyl ether (2×300 ml)
  5. extractionextracted with ethyl ether (2×200 ml)
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-393e56421b5849b3a7465315d500f1fe
出典データセット
uspto-grants-2008_01
特許番号
US07319104B2

関連ノート

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