Pyridine → HCID 58247781, compound

HRID 714289Notes

Reaction equation

HRID 714289 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[N:12]1[CH:17]=CC=CC=1.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.[OH2:31].[NH2:32]N>O1CCCC1.ClCCl>[NH:12]([C:17]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6])=[O:31])[NH2:32]

Participants

7

Reactant 4

HCID 1049PyridineHCID 24654Hydrazine hydrate (1:1)HCID 821294-Nitrophenyl chloroformateHCID 236984Methyl 2-aminopyridine-4-carboxylate

Product 1

HCID 58247781HCID 58247781, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-aminoisonicotinate (5.00 g, 32.9 mmol) and pyridine (3.90 g, 49.3 mmol) in anhydrous tetrahydrofuran (100 mL) and dichloromethane (100 mL) was added 4-nitrophenyl chloroformate (7.95 g, 39.4 mmol) at 0° C. The resulting solution was stirred for 1 hour at ambient temperature and filtered. The solid was washed with tetrahydrofuran (30 mL) and concentrated in vacuo to dryness. The residue was dissolved in tetrahydrofuran (40 mL), followed by the addition of hydrazine monohydrate (6.50 mL, 134.00 mmol). The mixture was stirred for 17 hours at ambient temperature and filtered. The solid was washed with water (20 mL) and ethyl acetate (20 mL) then dried in vacuo to give methyl 2-(hydrazinecarboxamido)isonicotinate as a yellowish solid (4.05 g, 59%): MS (ES+) m/z 211.1 (M+1).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with tetrahydrofuran (30 mL)
  3. concentrationconcentrated in vacuo to dryness
  4. dissolutionThe residue was dissolved in tetrahydrofuran (40 mL)
  5. stirringThe mixture was stirred for 17 hours at ambient temperature
  6. filtrationfiltered
  7. washThe solid was washed with water (20 mL) and ethyl acetate (20 mL)
  8. customthen dried in vacuo

Sources & evidence

ORD record
ord-6e8a1a005b584eafb9ebd17fb96ac81b
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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