Nitroethane → HCID 10453105, compound

HRID 1032726Notes

Reaction equation

HRID 1032726 reaction equation
[N+:1]([CH2:4][CH3:5])([O-:3])=O.C(N(CC)CC)C.[C:13]([C:15]1[CH:24]=[C:23]2[C:18]([C:19](=[O:37])[C:20]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:21][N:22]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:17][CH:16]=1)#[CH:14].C1(N=C=O)C=CC=CC=1>C(Cl)(Cl)Cl>[F:31][C:28]1[CH:27]=[CH:26][C:25]([N:22]2[C:23]3[C:18](=[CH:17][CH:16]=[C:15]([C:13]4[O:3][N:1]=[C:4]([CH3:5])[CH:14]=4)[CH:24]=3)[C:19](=[O:37])[C:20]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:21]2)=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 6587NitroethaneHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 10472113HCID 10472113, compound

Product 1

HCID 10453105HCID 10453105, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 9.8 g nitroethane and 13 ml triethylamine in 130 ml chloroform was added dropwise to a solution of 10.47 g ethyl 1,4-dihydro-7-ethynyl-1-(4- fluorophenyl)-4-oxo-3-quinolinecarboxylate and 15.5 g phenyl isocyanate in 80 ml chloroform over a period ofconcentrated in vacuo. The residue was crystallized in ether and recrystallized from acetonitrile to give 8.60 g ethyl 1,4-dihydro-1-(4-fluorophenyl)-7-(3-methyl-5-isoxazolyl)4 -oxo-3-quinolinecarboxylate (yellow solid, m.p. 214°-216° C.).

Workup

  1. customThe residue was crystallized in ether
  2. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-24de2d00b8224840befed0550e0ce613
Source dataset
uspto-grants-1990_09
Patent number
US04959363

Reaction notes

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