2-Methyl-2-butanol → HCID 178526251, 화합물

HRID 613379

반응식

HRID 613379 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 178526251HCID 178526251, 화합물수율 93%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21584188Chloroform methanol용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-b6960fd79dce4bc0b5a57ced0b12d413
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008213

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