Pyridine → HCID 54335057, compound

HRID 1604867Notes

Reaction equation

HRID 1604867 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([NH:9][NH2:10])=[O:8].N1C=CC=CC=1.[CH2:19]([O:21][C:22](Cl)=[O:23])[CH3:20]>CC(N(C)C)=O>[CH2:19]([O:21][C:22]([N:9]([C:7](=[O:8])[C:6]1[CH:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[OH:12])[NH2:10])=[O:23])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 27948705-chloro-2-hydroxybenzohydrazide

Product 1

HCID 54335057HCID 54335057, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

37.2 g of 5-chloro-2-hydroxybenzoic acid hydrazide are dissolved in 200 ml of dimethylacetamide and 16 g of pyridine and 22 g of chloroformic acid ethyl ester are added simultaneously over the course of 30 minutes. The reaction mixture is subsequently heated to 90° C for 3 hours whilst stirring, cooled and poured onto 1 litre of ice water. The precipitate which has separated out slowly crystallises throughout. The N-(5-chloro-2-hydroxybenzoyl)-hydrazinecarboxylic acid ethyl ester thus obtained (Stabiliser No. 11) is isolated, washed with water and recrystallised from ethanol. Melting point 172° C.

Workup

  1. temperaturecooled
  2. customThe precipitate which has separated out slowly
  3. customcrystallises throughout

Sources & evidence

ORD record
ord-5064085a7d1e44d1a35e1b1ee61d57f7
Source dataset
uspto-grants-1976_04
Patent number
US03948854

Reaction notes

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