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

HRID 714039Notes

Reaction equation

HRID 714039 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)-isoquinolinone

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 (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+, 1 Br).

Workup

  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

Sources & evidence

ORD record
ord-58ddefaa4e2f4d6a9677911f86f5e878
Source dataset
uspto-grants-2015_11
Patent number
US09187429B2

Reaction notes

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