Sodium Nitrite → 6-Fluoro-isoquinoline-3-carbonyl azide

HRID 340883Notes

Reaction equation

HRID 340883 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([C:12]([NH:14][NH2:15])=[O:13])=[CH:5]2.[N:16]([O-])=O.[Na+]>Cl.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][C:6]([C:12]([N:14]=[N+:15]=[N-:16])=[O:13])=[CH:5]2

Participants

5

Reactant 2

HCID 23668193Sodium Nitrite2×HCID 579481706-Fluoroisoquinoline-3-carbohydrazide

Product 1

HCID 579473966-Fluoro-isoquinoline-3-carbonyl azideYield 89%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Conditions

Temperature
2.5 °C

Procedure

To a suspension of 6-fluoro-isoquinoline-3-carboxylic acid hydrazide in HCl (1 N, 50 mL) and water (1 L) was added a solution of NaNO2 (11.4 g, 170 mmol, 1.5 eq) in water (100 mL) dropwise at 0-5° C. The mixture was stirred at 0-5° C. for 1 h. Another solution of NaNO2 (5.7 g, 85 mmol, 0.5 equiv.) in water (30 mL) was added and the reaction was stirred at 0-5° C. for 3 h until LC-MS indicated the completion of the reaction. The precipitate was filtered, washed with cold water, and dried under high vacuum to give 6-fluoro-isoquinoline-3-carbonyl azide as a light yellow solid (21.3 g, 89%). LRMS (M+H+) m/z 217.1.

Workup

  1. stirringthe reaction was stirred at 0-5° C. for 3 h 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-2a4d9b263af54068a3272ba262ed499f
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

Loading…