Sodium Nitrite → 3-Isoquinolinecarbonyl azide

HRID 340887Notes

Reaction equation

HRID 340887 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([NH:13][NH2:14])=[O:12])[N:2]=1.[N:15]([O-])=O.[Na+]>Cl.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([N:13]=[N+:14]=[N-:15])=[O:12])[N:2]=1

Participants

5

Reactant 2

HCID 23668193Sodium Nitrite2×HCID 55263898Isoquinoline-3-carbohydrazide

Product 1

HCID 579473563-Isoquinolinecarbonyl azideYield 93.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Conditions

Temperature
2.5 °C

Procedure

To a suspension of isoquinoline-3-carbohydrazide (43 g, 0.23 mol) in aqueous HCl (1 N, 230 mL) and water (1 L) was added a solution of NaNO2 (23.8 g, 0.34 mol) in water (200 mL) dropwise at 0-5° C. The mixture was stirred at 0-5° C. for 4 h. LC-MS indicated the reaction was not completed. Another solution of NaNO2 (11.9 g, 0.115 mol) in water (60 mL) was added and the reaction mixture was stirred at 0-5° C. until LC-MS indicated the completion of the reaction. The precipitate was filtered, washed with cold water, and dried under high vacuum to give isoquinoline-3-carbonyl azide (42.7 g, 93.8%) as a white solid. LRMS (M+H+) m/z 199.2.

Workup

  1. stirringthe reaction mixture was stirred at 0-5° C. until LC-MS
  2. customthe completion of the reaction
  3. filtrationThe precipitate was filtered
  4. washwashed with cold water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-a6dc436e86be451ba3129b7b174c2170
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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