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

HRID 530321

Reaktionsgleichung

Reaktionsgleichung von HRID 530321
[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

Komponenten

3

Edukt 2

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

Produkt 1

HCID 717433804-Bromo-6,7-dihydro-8(5H)-isoquinolinone

Versuchsvorschrift

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 (dark brown solution, no more SM visible on TLC). 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 washed with Et2O (2×) and CH2Cl2 (3×), the combined organic layers were dried over Na2SO4, filtered and concentrated to afford after high vacuum drying the title compound (4.30 g, 69%) as brown solid. MS: 226.0 (M+H+, 1Br).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 2.5 h (dark brown solution
  3. concentrationThe acidic solution was concentrated in vacuo
  4. temperaturecooled in ice
  5. washThe aqueous solution was washed with Et2O (2×) and CH2Cl2 (3×)
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford after high vacuum
  10. dry with materialdrying the title compound (4.30 g, 69%) as brown solid

Quellen und Nachweise

ORD-Eintrag
ord-8bd7b5c6578d400186f2c65f06cc38e6
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353081B2

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