Hydrazine hydrate (1:1) → 2-Methoxycarbonylpyridine-5-carboxylic acid hydrazide

HRID 842693

Reaction equation

HRID 842693 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([OH:13])=O)=[CH:7][N:6]=1)=[O:4].C(OC(N1C2C(=CC=CC=2)C=CC1OCC)=O)C.O.[NH2:33][NH2:34]>ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([NH:33][NH2:34])=[O:13])=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 5796316-(Methoxycarbonyl)pyridine-3-carboxylic acid

Product 1

HCID 187267762-Methoxycarbonylpyridine-5-carboxylic acid hydrazideYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-methoxycarbonylpyridine-5-carboxylic acid (Chem. Abstr., 68, 68840 h (1968)) (0.40 g, 2.2 mmol) and N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (0.60 g, 2.4 mmol) in dichloromethane (10 mL) was stirred at room temperature under nitrogen for 0.75 hour. Hydrazine hydrate (0.110 mL, 2.2 mmol) was then added and after a further 5 minutes the precipitate formed was collected by filtration, washed with dichloromethane and dried to give the title compound (0.349 g, 81%) as white solid, mp 177-180° C.

Workup

  1. customformed
  2. filtrationwas collected by filtration
  3. washwashed with dichloromethane
  4. customdried

Sources & evidence

ORD record
ord-095a2015d53c470ea27d57d4dcc1e1c0
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Linked notes

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