Hydrochloric Acid → 4-Bromo-6,7-dihydro-8(5H)-isoquinolinone

HRID 2277653

반응식

HRID 2277653 반응식
[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH:8](C(OC)=O)[C:7](=[O:16])[C:6]=2[CH:5]=[N:4][CH:3]=1.Cl>>[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7](=[O:16])[C:6]=2[CH:5]=[N:4][CH:3]=1

참가 물질

3

반응물 2

HCID 313Hydrochloric AcidHCID 86679925Methyl 4-bromo-8-oxo-5,6,7,8-tetrahydroisoquinoline-7-carboxylate

생성물 1

HCID 717433804-Bromo-6,7-dihydro-8(5H)-isoquinolinone수율 69.4%

실험 절차

The crude methyl 4-bromo-8-oxo-5,6,7,8-tetrahydroisoquinoline-7-carboxylate (7.79 g, 27.4 mmol) was dissolved (small amount of not dissolved material) in aq. 6M HCl (84.1 ml, 505 mmol) and heated at reflux for 2.5 h. The acidic solution was concentrated in vacuo, suspended in water (ca. 25 mL), cooled in ice and basified with 6.0 M KOH. The aqueous solution was extracted with ether (2×) and CH2Cl2 (3×), the combined organic layers were dried over Na2SO4, filtered and concentrated to afford the title compound (4.30 g, 69%) as a brown solid. MS: 226.0 (M+H+, 1Br).

후처리

  1. temperatureheated
  2. temperatureat reflux for 2.5 h
  3. concentrationThe acidic solution was concentrated in vacuo
  4. temperaturecooled in ice and basified with 6.0 M KOH
  5. extractionThe aqueous solution was extracted with ether (2×) and CH2Cl2 (3×)
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b4c0d610aadc477a800985f328480d41
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133158B2

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