Acetic Acid → HCID 57440940, compound

HRID 1819767Notes

Reaction equation

HRID 1819767 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[C:18]([Cl:25])[C:3]=1[O:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2.[CH3:26]C(O)=O>C1COCC1.CCOCC>[CH3:26][O:16][C:15]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[N:7]=[CH:6][C:5]([O:4][C:3]1[C:18]([Cl:25])=[CH:19][C:20]([N+:22]([O-:24])=[O:23])=[CH:21][C:2]=1[Cl:1])=[CH:14]2)=[O:17]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 22148882HCID 22148882, compound

Product 1

HCID 57440940HCID 57440940, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2,6-Dichloro-4-nitro-phenoxy)-quinoline-6-carboxylic acid (94) (443 mg, 0.93 mmol) in dry THF (20 mL) was added CH2N2 in Et2O solution [Prepared from nitrosomethylurea (1.65 g) and 50% KOH (5 mL)]. This mixture was stirred at room temperature for 1 h. AcOH (1 mL) was added to the reaction mixture, which was then concentrated. Sat NaHCO3 was added to the residue, which was extracted twice with AcOEt. Organic layer was washed by brine, dried over anhydrous MgSO4, and concentrated to afford compound 95 (415 mg). 1H NMR (300 MHz, DMSO-d6) δ 3.89 (3H, s), 5.75 (2H, br s), 6.76 (2H, s), 7.73 (1H, d, J=2.9 Hz), 8.09 (2H, s), 8.67 (1H, s), 8.94 (1H, d, J=2.9 Hz).

Workup

  1. concentrationwas then concentrated
  2. additionSat NaHCO3 was added to the residue, which
  3. extractionwas extracted twice with AcOEt
  4. washOrganic layer was washed by brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-72a4656b32f44a298e790e813e717cc9
Source dataset
uspto-grants-2009_10
Patent number
US07601841B2

Reaction notes

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