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

HRID 2277653

Reaction equation

HRID 2277653 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b4c0d610aadc477a800985f328480d41
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Linked notes

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