Sulfuric Acid → 7-Bromoisoquinolin-3-amine

HRID 468720Notes

Reaction equation

HRID 468720 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]=1C#N)=[CH:9][CH:8]=[C:7]([Br:14])[CH:6]=2.OS(O)(=O)=O.[OH-].[Na+]>O>[Br:14][C:7]1[CH:6]=[C:5]2[C:10]([CH:11]=[C:2]([NH2:1])[N:3]=[CH:4]2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 679748233-Amino-7-bromoisoquinoline-4-carbonitrile

Product 1

HCID 529877577-Bromoisoquinolin-3-amineYield 19%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

To a stirred solution of 3-amino-7-bromoisoquinoline-4-carbonitrile (25 g, 101 mmol) in water (100 mL) was added H2SO4 (100 mL) dropwise while cooling in an ice-water bath. Then the mixture was stirred and heated to 115° C. for 3 days. After that, the reaction was cooled down to 0° C. 10 M aqueous NaOH was added to adjust to pH>12. The resulting solid precipitate was collected by filtration, washed with water, and dried under vacuum to yield 4.2 g (19%) of 7-bromo-isoquinolin-3-amine. LCMS (ESI): M+H=222.8; 1H NMR (400 MHz, DMSO-d6) δ 8.76 (s, 1H), 8.00 (t, J=0.8 Hz, 1H), 7.49-7.48 (m, 2H), 6.58 (s, 1H), 6.06 (s, 1H).

Workup

  1. temperaturewhile cooling in an ice-water bath
  2. temperatureAfter that, the reaction was cooled down to 0° C
  3. filtrationThe resulting solid precipitate was collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-282737dab1234efca67bb8861e8eae5a
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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