4-Amino-3,5-dimethylisoxazole → (6-Bromo-3-nitro-quinolin-4-yl)-(3,5-dimethyl-isoxazol-4-yl)-amine

HRID 445543Notes

Reaction equation

HRID 445543 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2Cl.[CH3:16][C:17]1[C:21]([NH2:22])=[C:20]([CH3:23])[O:19][N:18]=1>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2[NH:22][C:21]1[C:17]([CH3:16])=[N:18][O:19][C:20]=1[CH3:23]

Participants

4

Reactant 2

HCID 1820404-Amino-3,5-dimethylisoxazoleHCID 219841286-Bromo-4-chloro-3-nitroquinoline

Product 1

HCID 59620045(6-Bromo-3-nitro-quinolin-4-yl)-(3,5-dimethyl-isoxazol-4-yl)-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6-bromo-4-chloro-3-nitro-quinoline (Stage A.4, 1.1 g, 3.83 mmol) and 3,5-dimethyl-4-aminoisoxazol (Aldrich, Buchs, Switzerland, 472 mg, 4.21 mmol) in acetic acid (10 ml) was stirred at it for 4 h. Then the RM was quenched with H2O (40 ml). The suspension was filtered, the solid cake was washed with H2O (2×) and dried under vacuum, before being dissolved in EtOAc. The solution was washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered and evaporated to dryness to give the title compound as an orange solid (HPLC tR 2.96 min (Method A); M+H=363, 365; M−H=361, 363 MS-ES).

Workup

  1. customThen the RM was quenched with H2O (40 ml)
  2. filtrationThe suspension was filtered
  3. washthe solid cake was washed with H2O (2×)
  4. customdried under vacuum
  5. dissolutionbefore being dissolved in EtOAc
  6. washThe solution was washed with saturated aqueous NaHCO3
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-45ee0e84efc04c518f4d962beb33716d
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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