tert-Butyl carbazate → 2-tert-butoxycarbonyl-2,3-dihydro-6-nitro-1H-pyrazolo[4,3-c]quinolin-3-one

HRID 613472Notes

Reaction equation

HRID 613472 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17]CC)=O.[C:20]([O:24][C:25]([NH:27][NH2:28])=[O:26])([CH3:23])([CH3:22])[CH3:21]>O1CCOCC1>[C:20]([O:24][C:25]([N:27]1[C:15](=[O:17])[C:3]2[CH:4]=[N:5][C:6]3[C:7]([N+:12]([O-:14])=[O:13])=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]=2[NH:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 11196760Ethyl 4-chloro-8-nitroquinoline-3-carboxylate

Product 1

HCID 195930092-tert-butoxycarbonyl-2,3-dihydro-6-nitro-1H-pyrazolo[4,3-c]quinolin-3-oneYield 77.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 4-chloro-3-ethoxycarbonyl-8-nitroquinoline (500 mg) and tert-butoxycarbonylhydrazine (283 mg) in dioxane was refluxed for 1 hour. The mixture was concentrated in vacuo to give 2-tert-butoxycarbonyl-2,3-dihydro-6-nitro-1H-pyrazolo[4,3-c]quinolin-3-one (458 mg).

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-a024566ab13248299f0b48d845e13f21
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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