1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Chloropyridine-4-carbohydrazide

HRID 732028Notes

Reaction equation

HRID 732028 reaction equation
C1C=CC2N(O)[N:8]=[N:7]C=2C=1.CCN=C=NCCCN(C)C.[Cl:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][N:31]=1)[C:26](O)=[O:27].O.NN>C(#N)C>[Cl:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][N:31]=1)[C:26]([NH:7][NH2:8])=[O:27]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 24654Hydrazine hydrate (1:1)HCID 757711-HydroxybenzotriazoleHCID 2369852-Chloroisonicotinic acid

Product 1

HCID 2362062-Chloropyridine-4-carbohydrazideYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

HOBt (823 mg, 6.09 mmol), and EDCI (1.2 g, 6.09 mmol) were added to a suspension of 2-chloro-isonicotinic acid (800 mg, 5.08 mmol) in acetonitrile (10.3 ml) at room temperature. After two h a solution of hydrazine monohydrate (0.493 ml, 10.2 mmol) in acetonitrile (5.0 ml) was added drop-wise at 0° C. After 30 min, the solvent was removed using a roto-evaporator and the residue was diluted with ethyl acetate, quenched with water, dried over sodium sulfate, filtered and concentrated to afford 2-chloro-isonicotinic acid hydrazide (493 mg, 57%, yellow solid). 1H NMR (DMSO) d (ppm): 10.21 (bs, 1H), 8.55 (d, 1H), 7.82 (s, 1H), 7.75 (d, 1H), 4.69 (bs, 2H).

Workup

  1. customthe solvent was removed
  2. customa roto-evaporator
  3. additionthe residue was diluted with ethyl acetate
  4. customquenched with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6195c49a2d83482288574045f9e2e352
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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