7,8-Dihydroisoquinolin-5(6H)-one--hydrogen chloride (1/1) → HCID 68707913, compound

HRID 222119Notes

Reaction equation

HRID 222119 reaction equation
Cl.[CH:2]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7](=[O:12])[C:6]=2[CH:5]=[CH:4][N:3]=1.C1C=C[NH+]=CC=1.[Br:19][Br-]Br>C(O)(=O)C>[BrH:19].[Br:19][CH:8]1[CH2:9][CH2:10][C:11]2[CH:2]=[N:3][CH:4]=[CH:5][C:6]=2[C:7]1=[O:12]

Participants

3

Reactant 1

HCID 231571667,8-Dihydroisoquinolin-5(6H)-one--hydrogen chloride (1/1)

Product 1

HCID 68707913HCID 68707913, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 7,8-dihydro-6H-isoquinolin-5-one 8A (13.3 mmol) and pyridinium bromide perbromide (13.3 mmol) were suspended in glacial acetic acid (15 mL), and heated to 100° C. with microwave irradiation for 15 min. The solid formed was filtered to give the title compound as a yellow solid in 83% yield. ESI (+) MS: m/z 227 (MH+). 1H NMR: 2.39-2.62 (m, 2H), 3.00-3.15 (m, 2H), 4.43 (dd, J=12.50, 4.94, 1H), 7.72-7.83 (m, 1H), 8.61-8.74 (m, 1H), 8.75-8.85 (m, 1H).

Workup

  1. customThe solid formed
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-24e33f1a27c44a2e90e6767aac656232
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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