Chloroform → 8-(3-Amino-2,6-dimethylbenzyloxy)-2-methylquinoline

HRID 1699172ノート

反応式

HRID 1699172 の反応式
[CH3:1][C:2]1[C:20]([N+:21]([O-])=O)=[CH:19][CH:18]=[C:17]([CH3:24])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2.O.NN.C(Cl)(Cl)Cl>CO>[NH2:21][C:20]1[C:2]([CH3:1])=[C:3]([C:17]([CH3:24])=[CH:18][CH:19]=1)[CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[C:13]([CH3:16])[CH:12]=[CH:11]2

参加物

5

反応物 3

HCID 6212ChloroformHCID 24654Hydrazine hydrate (1:1)HCID 183218528-(2,6-Dimethyl-3-nitrobenzyloxy)-2-methylquinoline

生成物 1

HCID 183218048-(3-Amino-2,6-dimethylbenzyloxy)-2-methylquinoline収率 78.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a suspension of 8-(2,6-dimethyl-3-nitrobenzyloxy)-2-methylquinoline (2.34 g), ferric chloride (70.6 mg) and carbon (70.6 mg) in methanol (35 ml) was added hydrazine monohydrate (1.09 g) at 65° C., and the mixture was refluxed for 2 hours. Methanol (20 ml) was added thereto, and the mixture was refluxed for 1 hour. After cooling chloroform was added thereto, and the resulting precipitates were filtered off. The filtrate was concentrated and the residue was dissolved in chloroform. The solution was washed with saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate and concentrated. The residue was crystallized with ethyl acetate to give 8-(3-amino-2,6-dimethylbenzyloxy)-2-methylquinoline (1.67 g) as a pale brown crystal.

後処理

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperaturethe mixture was refluxed for 1 hour
  3. additionwas added
  4. customthe resulting precipitates
  5. filtrationwere filtered off
  6. concentrationThe filtrate was concentrated
  7. dissolutionthe residue was dissolved in chloroform
  8. washThe solution was washed with saturated sodium bicarbonate solution, water and brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was crystallized with ethyl acetate

出典と根拠

ORDレコード
ord-71dd8e115c8a4e3f8d7478c62fde2609
出典データセット
uspto-grants-2002_02
特許番号
US06344462B1

反応ノート

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