Hydrochloric Acid → HCID 57947477, compound

HRID 340924Notes

Reaction equation

HRID 340924 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[N:8][CH:9]=2)[CH:4]=[C:3]([C:11]([O-:13])=O)[N:2]=1.[NH2:14][NH2:15].Cl.[N:17]([O-])=O.[Na+].C([O-])(O)=O.[Na+]>O.C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[N:8][CH:9]=2)[CH:4]=[C:3]([C:11]([N:14]=[N+:15]=[N-:17])=[O:13])[N:2]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 86635661HCID 86635661, compound

Product 1

HCID 57947477HCID 57947477, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2,7-naphthyridine-3-carboxylate (260 mg, 1.29 mmol), hydrazine (0.20 mL, 6.44 mmol) and ethanol was refluxed for 2 h and concentrated to dryness. The resulting residue was mixed with 2N HCl (1.3 mL, 2.60 mmol) and H2O (5 mL) and cooled with an ice bath. To the mixture was added a solution of NaNO2 (178 mg, 2.6 mmol in 1 mL H2O) dropwise, the mixture was stirred at 0° C. for 1 h. The mixture was then neutralized with saturated NaHCO3 and extracted with DCM. The DCM solution was washed with water, brine, dried and concentrated to give 2,7-naphthyridine-3-carbonyl azide as a pale yellow solid (244 mg, 95%). LRMS (M−N2+H+) m/z 172.1.

Workup

  1. temperaturewas refluxed for 2 h
  2. concentrationconcentrated to dryness
  3. temperaturecooled with an ice bath
  4. extractionextracted with DCM
  5. washThe DCM solution was washed with water, brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-743436e0de454548a08886e11bb7a28a
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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