Acetic Acid → 4-Bromo-5,6,7,8-tetrahydroisoquinolin-8-OL

HRID 530369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530369
[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7](=[O:12])[C:6]=2[CH:5]=[N:4][CH:3]=1.[BH4-].[Na+].CC(O)=O>CO>[Br:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH:7]([OH:12])[C:6]=2[CH:5]=[N:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 717433804-Bromo-6,7-dihydro-8(5H)-isoquinolinone

Produkt 1

HCID 717438914-Bromo-5,6,7,8-tetrahydroisoquinolin-8-OLAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of 4-bromo-6,7-dihydroisoquinolin-8(5H)-one (intermediate A-2 [C]) (2.135 g, 9.44 mmol) in MeOH (18.9 mL) was cooled to 0° C. and treated with NaBH4 (357 mg, 9.44 mmol) in 5 portions over 30 min. The reaction was stirred for ¾ h at 0° C., then AcOH was added dropwise until a pH ˜5-6 was obtained and the reaction mixture was evaporated. The residue was diluted with water and poured into aq. sat. NaHCO3-solution, then extracted with EtOAc (3×). The organic layers are washed once with aq. sat. NaHCO3 and aq. 10% NaCl solution, dried over Na2SO4 and concentrated in vacuo. The residue was precipitated with CH2Cl2/n-pentane to afford the title compound (1.98 g, 92%) as dark brown viscous oil. MS: 227 (M+, 1Br).

Aufarbeitung

  1. customwas obtained
  2. customthe reaction mixture was evaporated
  3. additionThe residue was diluted with water
  4. additionpoured into aq. sat. NaHCO3-solution
  5. extractionextracted with EtOAc (3×)
  6. washThe organic layers are washed once with aq. sat. NaHCO3 and aq. 10% NaCl solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was precipitated with CH2Cl2/n-pentane

Quellen und Nachweise

ORD-Eintrag
ord-72e64597de804e79a639fa30212405e9
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353081B2

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