(4-Chlorophenyl)hydrazine → HCID 178486389, compound

HRID 1633253Notes

Reaction equation

HRID 1633253 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[N:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18]CC)=O.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][NH2:29])=[CH:24][CH:23]=1>C1(C)C(C)=CC=CC=1>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[C:16](=[O:18])[C:3]3=[CH:4][NH:5][C:6]4[C:7]([O:14][CH3:15])=[N:8][C:9]([O:12][CH3:13])=[CH:10][C:11]=4[C:2]3=[N:29]2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 70624(4-Chlorophenyl)hydrazineHCID 13377407HCID 13377407, compound

Product 1

HCID 178486389HCID 178486389, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 2.25 g of ethyl 4-chloro-6,8-dimethoxy-1,7-naphthyridin-3-carboxylate and 1.2 g of p-chlorophenylhydrazine in 180 ml of xylene is heated at reflux overnight, then cooled and extracted with 1N sodium hydroxide (300 ml). The aqueous alkali phase is separated, washed with ether and neutralized with 20 g of ammonium chloride to precipitate a solid. The solid is collected and washed with ethanol to yield 2-(4-chlorophenyl)-6,8-dimethoxy-pyrazolo[4,3-c][1,7]naphthyridin-3(5H)-one, m.p. 318°-321°.

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. temperaturecooled
  4. extractionextracted with 1N sodium hydroxide (300 ml)
  5. customThe aqueous alkali phase is separated
  6. washwashed with ether and neutralized with 20 g of ammonium chloride
  7. customto precipitate a solid
  8. customThe solid is collected
  9. washwashed with ethanol

Sources & evidence

ORD record
ord-5f005a9dc9674ebc9563467ea247d96c
Source dataset
uspto-grants-1984_10
Patent number
US04479955

Reaction notes

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