Water → 7-Azidoisoquinoline

HRID 1768100Notes

Reaction equation

HRID 1768100 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.N([O-])=O.[Na+].O.[N-:17]=[N+:18]=[N-].[Na+]>C(O)(C(F)(F)F)=O>[N:1]([C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1)=[N+:17]=[N-:18]

Participants

6

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 14660277Isoquinolin-7-amineHCID 23668193Sodium Nitrite

Product 1

HCID 222807507-AzidoisoquinolineYield 90.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 7-aminoisoquinoline (7.0 g) in TFA (35 mL) at 0° C. was added sodium nitrite (4.02 g) portionwise over a period of 30 minutes. The reaction was stirred at 0° C. to room temperature for 1.5 h. Water (3.5 mL) was added followed by portionwise addition of sodium azide (3.48 g) at 0° C. over a period of 30 minutes. After the addition, the reaction was slowly warmed up to room temperature and stirred for 1 h. Two third of TFA was evaporated and the residue was cooled to 0° C. Sodium bicarbonate (sat. in water) was added dropwisely to the residue until the pH was abouty 8–9. After extraction with methylene chloride (4×60 mL), the organic phase was combined, washed with water, brine, dried over sodium sulfate, filtered and concentrated to leave 7-azidoisoquinoline (7.5 g) as a dark brown solid. CI mass spectrum z (rel. intensity) 171 (M+H, 100).

Workup

  1. additionAfter the addition
  2. stirringstirred for 1 h
  3. customTwo third of TFA was evaporated
  4. temperaturethe residue was cooled to 0° C
  5. additionSodium bicarbonate (sat. in water) was added dropwisely to the residue until the pH
  6. extractionAfter extraction with methylene chloride (4×60 mL)
  7. washwashed with water, brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-3a329104e59046c1b5775e304aad6210
Source dataset
uspto-grants-2007_06
Patent number
US07235575B2

Reaction notes

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