2-Cyanobenzeneacetonitrile → 1-Bromoisoquinolin-3-amine

HRID 1814588Notes

Reaction equation

HRID 1814588 reaction equation
[C:1]([CH2:3][C:4]1[C:5]([C:10]#[N:11])=[CH:6][CH:7]=[CH:8][CH:9]=1)#[N:2].[BrH:12].C([O-])(=O)C>C(O)(=O)C>[NH2:2][C:1]1[N:11]=[C:10]([Br:12])[C:5]2[C:4]([CH:3]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 773682-CyanobenzeneacetonitrileHCID 20344520Hydrogen bromide acetate

Product 1

HCID 2898451-Bromoisoquinolin-3-amineYield 90.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of α-cyanotolunitrile (20.0 g) in acetic acid (50 ml) was added 25% hydrogen bromide/acetate solution (150 ml), and the mixture was reacted at room temperature overnight. The resulting precipitates were collected by filtration and then added to a 10% aqueous solution of potassium carbonate. The yellow powder was changed to a pale yellow powder. The resulting powder was collected by filtration, washed with water and hexane, and dried at 50° C. under reduced pressure, to give 3-amino-1-bromoisoquinoline (28.5 g; 90.8%).

Workup

  1. customthe mixture was reacted at room temperature overnight
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. additionadded to a 10% aqueous solution of potassium carbonate
  5. filtrationThe resulting powder was collected by filtration
  6. washwashed with water and hexane
  7. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-7cbcd151018848d4b441dbf2af787954
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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