2-Methyl-2-butanol → HCID 178526251、化合物

HRID 613379

反応式

HRID 613379 の反応式
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8].[NH2:9][CH2:10][CH2:11][CH2:12][OH:13].C([O-])(O)=O.[Na+].C(O)(CC)(C)C>C(Cl)Cl.CO.C(Cl)(Cl)Cl>[OH:13][CH2:12][CH2:11][CH2:10][NH:9][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:8]

参加物

7

反応物 4

HCID 64052-Methyl-2-butanolHCID 90863-Amino-1-propanolHCID 754652-Chloropyridine oxideHCID 516892Sodium Bicarbonate

生成物 1

HCID 178526251HCID 178526251、化合物収率 93%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21584188Chloroform methanol溶媒

実験手順

A mixture of 2-chloropyridine-N-oxide (16.6 g, 0.1 mole), 3-amino-1-propanol (15.3 mL, 0.2 mole), NaHCO3 (42 g, 0.5 mole), and tert-amyl alcohol (100 mL) was heated to reflux. After 21 hr, the reaction was cooled, diluted with CH2Cl2 (300 mL), and suction filtered to remove insoluble materials. The filtrate was concentrated and reconcentrated from toluene to leave a yellow oil. Silica gel chromatography (20% MeOH/CHCl3) gave the title compound (15.62 g, 93%) as a yellow solid: TLC (20% MeOH/CHCl3) Rf 0.48; 1H NMR (250, CDCl3) δ 8.07 (dd, J=6.6, 1.2 Hz, 1 H), 7.34 (br t, 1 H), 7.10-7.30 (m, 1 H), 6.64 (dd, J=8.5, 1.4 Hz, 1 H), 6.40-6.60 (m, 1 H), 4.49 (br s, 1 H), 3.65-3.90 (m, 2 H), 3.35-3.60 (m, 2 H), 1.75-2.00 (m, 2 H); MS (ES) m/e 169 (M+H)+.

後処理

  1. temperaturewas heated to reflux
  2. temperaturethe reaction was cooled
  3. filtrationfiltered
  4. customto remove insoluble materials
  5. concentrationThe filtrate was concentrated
  6. customto leave a yellow oil

出典と根拠

ORDレコード
ord-b6960fd79dce4bc0b5a57ced0b12d413
出典データセット
uspto-grants-1999_12
特許番号
US06008213

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