Hydrochloric Acid → 3-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazole-5-carbaldehyde

HRID 1245393Notes

Reaction equation

HRID 1245393 reaction equation
C[O:2][CH:3](OC)[CH:4]1[O:8][N:7]=[C:6]([C:9]2[CH:27]=[CH:26][C:12]([O:13][CH2:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=[C:17]([CH3:25])[CH:16]=3)=[CH:11][CH:10]=2)[CH2:5]1.Cl>C1COCC1>[CH3:25][C:17]1[CH:16]=[C:15]([CH2:14][O:13][C:12]2[CH:26]=[CH:27][C:9]([C:6]3[CH2:5][CH:4]([CH:3]=[O:2])[O:8][N:7]=3)=[CH:10][CH:11]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 219111774-[4-(5-Dimethoxymethyl-4,5-dihydro-isoxazol-3-yl)-phenoxymethyl]-2-methyl-quinoline

Product 1

HCID 218980783-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazole-5-carbaldehydeYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from step 10a (0.4 g, 1.0 mmol) was dissolved in THF (5 mL) and 6 N HCl (5 mL) and heated to 60° C. for 2.5 h. The reaction was cooled and concentrated, and the aqueous layer was neutralized with NaOH and then extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The oil was purified with FCC eluting ethyl acetate:methylene chloride (80:20) to give 3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazole-5-carbaldehyde (0.1 g, 72%) as an oil. MS found: (M+H)+=347.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give an oil
  8. customThe oil was purified with FCC
  9. washeluting ethyl acetate:methylene chloride (80:20)

Sources & evidence

ORD record
ord-46d410f93ad44a7c80801e13609bacd7
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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