Acetic Acid → 6-Bromoisoquinolin-1(2H)-one

HRID 906398Notes

Reaction equation

HRID 906398 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5](C#N)=[C:4](/[CH:10]=[CH:11]/[N:12]([CH3:14])C)[CH:3]=1.C(O)(=[O:17])C>Br.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:8][CH:9]=1)[C:14](=[O:17])[NH:12][CH:11]=[CH:10]2

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 57453860HCID 57453860, compound

Product 1

HCID 158851826-Bromoisoquinolin-1(2H)-one

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

A solution of 4-bromo-2-[(E)-2-(dimethylamino)ethenyl]benzonitrile (Example 1a, 1.0 g) in 33% Hydrobromic acid in acetic acid (10 mL) under nitrogen was stirred at 80° C. for 4 h. The reaction mixture was diluted with water (250 mL), and the brown solid was filtered off, washed with diethyl ether and dried to afford the subtitle compound (0.70 g) as a solid.

Workup

  1. filtrationthe brown solid was filtered off
  2. washwashed with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-dcaafab239a04d918025c998de600e2e
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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