Ethanol → Ethyl 1-amino-2,3-dihydro-1H-indene-1-carboxylate

HRID 884009노트

반응식

HRID 884009 반응식
S(Cl)(Cl)=O.[NH2:5][C:6]1([C:15]([OH:17])=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1.[CH2:18](O)[CH3:19]>>[NH2:5][C:6]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1

참가 물질

4

반응물 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 2338101-Amino-2,3-dihydro-1H-indene-1-carboxylic acid

생성물 1

HCID 14244939Ethyl 1-amino-2,3-dihydro-1H-indene-1-carboxylate수율 84%

실험 절차

Thionyl chloride (0.617 mL, 8.465 mmol) was added dropwise to anhydrous ethanol (6 mL) cooled to −30° followed by 1-amino-2,3-dihydro-1H-indene-1-carboxylic acid (0.300 g, 1.693 mmol) the reaction was then refluxed for 4 hours. The reaction was concentrated by rotary evaporation and diluted with water (5 mL) and the pH was adjusted to 9 with 6N aqueous sodium hydroxide. The solution was extracted with ethyl acetate (2×25 mL) and the organic extracts were washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated by rotary evaporation to afford the title compound as an oil (0.293 g, 1.43 mmol, 84%). 1H NMR (300 MHz, DMSO-D6) □ ppm 1.12 (t, J=7.17 Hz, 3 H) 1.85-2.07 (m, 1 H) 2.31 (s, 2 H) 2.51-2.66 (m, 1 H) 2.93 (t, J=6.99 Hz, 2 H) 3.90-4.21 (m, 2 H) 7.13-7.34 (m, 4 H). MS (DCI) m/z 206 (M+H)+, 223 (M+NH4)+.

후처리

  1. temperaturecooled to −30°
  2. temperaturewas then refluxed for 4 hours
  3. concentrationThe reaction was concentrated by rotary evaporation
  4. additiondiluted with water (5 mL)
  5. extractionThe solution was extracted with ethyl acetate (2×25 mL)
  6. washthe organic extracts were washed with brine (25 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporation

출처 및 근거

ORD 기록
ord-70219fb937d34e158c9281f8b44cd48a
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236950B2

반응 노트

불러오는 중…