Hydrochloric Acid → 4-(5-(4-(Pentyloxy)phenyl)-3-isoxazolyl)benzoic acid

HRID 1408301Notes

Reaction equation

HRID 1408301 reaction equation
[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:27])[CH2:14][C:15]([C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=2)=O)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[Na+].Cl.[NH2:31]O.Cl>C(O)C.O>[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:27][N:31]=[C:15]([C:17]3[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)[CH:14]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 11405985Methyl 4-[1,3-dioxo-3-[4-(pentyloxy)phenyl]propyl]benzoate

Product 1

HCID 99752244-(5-(4-(Pentyloxy)phenyl)-3-isoxazolyl)benzoic acidYield 23.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To 92 mg (0.26 mmol) methyl 4-[3-(4-pentyloxyphenyl)-3-oxopropanoyl]benzoate in 10 mL ethanol was added 146 mg (3.63 mmol) sodium hydroxide and 500 mg (7.25 mmol) hydroxylamine hydrochloride in 2 mL water. The solution was refluxed for 7 h. After cooling to room temperature, 1 M hydrochloric acid was added and the precipitate formed was filtered off and washed with water. Upon drying, the product was obtained as a white solid (22 mg, 0.06 mmol, 23%). 1H NMR (D6-acetone, 500 MHz): δ=8.18 (d, 2H, J=8.6 Hz), 8.06 (d, 2H, J=8.5 Hz), 7.89 (d, 2H, J=8.6 Hz), 7.30 (s, 1H), 7.11 (d, 2H, J=8.6 Hz), 4.08 (t, 2H, J=7.3 Hz), 1.82 (m, 2H), 1.47 (m, 4H), 0.93 (t, 3H, J=7.3 Hz). HPLC: 4.641 min.

Workup

  1. temperatureThe solution was refluxed for 7 h
  2. customthe precipitate formed
  3. filtrationwas filtered off
  4. washwashed with water
  5. customUpon drying

Sources & evidence

ORD record
ord-243af59e694b4c7ab7555d4db304f19f
Source dataset
uspto-grants-2014_12
Patent number
US08921309B2

Reaction notes

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