Hydrochloric Acid → Methyl 4-[5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylate

HRID 576038Notes

Reaction equation

HRID 576038 reaction equation
[OH-:1].[Na+].S(O)(O)(=O)=O.[NH2:8]O.NO.[F:12][C:13]([F:47])([F:46])[C:14]1[CH:15]=[C:16]([C:24]([C:42]([F:45])([F:44])[F:43])=[CH:25][C:26]([C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]([C:38]([O:40][CH3:41])=[O:39])=[CH:30][CH:29]=2)=O)[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1.Cl>O.O1CCCC1>[F:22][C:20]([F:23])([F:21])[C:18]1[CH:17]=[C:16]([C:24]2([C:42]([F:45])([F:43])[F:44])[O:1][N:8]=[C:26]([C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:31]([C:38]([O:40][CH3:41])=[O:39])=[CH:30][CH:29]=3)[CH2:25]2)[CH:15]=[C:14]([C:13]([F:12])([F:46])[F:47])[CH:19]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 159255Hydroxylamine, sulfate (1:1)HCID 75153691HCID 75153691, compound

Product 1

HCID 46222620Methyl 4-[5-[3,5-bis(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (50%, 1.53 g, 38.2 mmol) was added to hydroxylamine sulfate (1.57 g, 9.57 mmol) in water (18 mL). A portion of the solution (˜51%, ˜9.8 mmol of hydroxylamine) was added dropwise to methyl 4-[3-[3,5-bis(trifluoromethyl)phenyl]-4,4,4-trifluoro-1-oxo-2-buten-1-yl]-1-naphthalenecarboxylate (i.e. the product of Step A) (5.00 g, 9.61 mmol) in tetrahydrofuran (45 mL). After ˜45 min the mixture was poured into hydrochloric acid (1 N, 100 mL) and was extracted with ether (3×80 mL).

Workup

  1. extractionwas extracted with ether (3×80 mL)

Sources & evidence

ORD record
ord-68d6854821d24925b3f0bfaa28102a4f
Source dataset
uspto-grants-2015_05
Patent number
US09035101B2

Reaction notes

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