Phenylhydrazine → N'-phenyl-2-pyridin-4-ylacetohydrazide

HRID 1867612Notes

Reaction equation

HRID 1867612 reaction equation
Cl.CN(C)CCCN=C=NCC.O.N1(O)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[N:15]1.C(N(CC)C(C)C)(C)C.C1(NN)C=CC=CC=1.Cl.[N:42]1[CH:47]=[CH:46][C:45]([CH2:48][C:49](O)=[O:50])=[CH:44][CH:43]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.ClCCl>[C:17]1([NH:16][NH:15][C:49](=[O:50])[CH2:48][C:45]2[CH:46]=[CH:47][N:42]=[CH:43][CH:44]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

9

Reactant 6

HCID 7516PhenylhydrazineHCID 810974-Pyridineacetic acid hydrochlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 68566518N'-phenyl-2-pyridin-4-ylacetohydrazideYield 19.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (2.06 g, 10.76 mmol, 2.02 mmol), 1H-1,2,3-benzotriazol-1-ol hydrate (1.45 g, 10.76 mmol), N,N-diisopropylethylamine (4.69 mL, 26.9 mmol), and phenyl hydrazine (970 mg, 8.97 mmol) were added to a solution of 4-pyridylacetic acid hydrochloride (1.23 g, 8.97 mmol) in dimethylformamide (10 mL). After 16 h, the reaction was worked up with dichloromethane and saturated sodium bicarbonate. The organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (99% dichloromethane→12% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (400 mg). MS 228.5 (M+1)

Workup

  1. washThe organic extracts were washed with brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (99% dichloromethane→12% methanol {1% ammonium hydroxide}/dichloromethane)

Sources & evidence

ORD record
ord-f205cadb48294561bdc0a579afa19181
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

Loading…