(4-Chlorophenyl)hydrazine → HCID 178473318, compound

HRID 1194526Notes

Reaction equation

HRID 1194526 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:15][CH2:14][C:13]2[N:12]=[CH:11][C:10]([C:16]([O:18]CC)=O)=[C:9](Cl)[C:8]=2[CH2:7]1)=[O:5])[CH3:2].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][NH2:30])=[CH:25][CH:24]=1>C(O)CCC>[CH2:1]([O:3][C:4]([N:6]1[CH2:15][CH2:14][C:13]2[NH:12][CH:11]=[C:10]3[C:16](=[O:18])[N:29]([C:26]4[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=4)[N:30]=[C:9]3[C:8]=2[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 70624(4-Chlorophenyl)hydrazineHCID 13713226HCID 13713226, compound

Product 1

HCID 178473318HCID 178473318, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3 g of ethyl 6-ethoxycarbonyl-4-chloro-5,6,7,8-tetrahydro[1,6]naphthyridine-3-carboxylate (Example 1c) and 1.4 g of p-chlorophenylhydrazine in 100 mL of n-butanol is stirred and heated at reflux under nitrogen atmosphere for 20 hours, then cooled. Solid is collected and washed successively with n-butanol, then with ether. Solid is then dried in a vacuum oven at 80° for 24 hours obtaining 8-ethoxycarbonyl-2-p-chlorophenyl-2,3,6,7,8,9-hexahydropyrazolo[4,3-c][1,6]naphthyridine-3(5H)-one, mp 357°-359°.

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen atmosphere for 20 hours
  3. temperaturecooled
  4. customSolid is collected
  5. washwashed successively with n-butanol
  6. customSolid is then dried in a vacuum oven at 80° for 24 hours

Sources & evidence

ORD record
ord-ca3fa3c31b694a618aa7bcbbd99b59c7
Source dataset
uspto-grants-1989_03
Patent number
US04814450

Reaction notes

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