Hydrochloric Acid → HCID 42596963, compound

HRID 332573Notes

Reaction equation

[F:1][C:2]1[C:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[CH:14][CH:13]=[C:12]([O:24][CH3:25])[C:3]=1[O:4][C:5]1[CH:6]=[C:7](N)[CH:8]=[CH:9][CH:10]=1.N([O-])=O.[Na+].[ClH:30]>O.[Cu]Cl>[Cl:30][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[O:4][C:3]1[C:2]([F:1])=[C:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH:14]=[CH:13][C:12]=1[O:24][CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 250 mL flask which contained the suspension of 3-[2-fluoro-3-(4-fluoro-benzyl)-6-methoxy-phenoxy]-phenylamine (P-02) (135 mg, 0.4 mmole) in aq HCl (12 N. 5 mL) was slowly added the solution of sodium nitrite (50 mg, 0.7 mmole) in water (3 mL) at 0° C. The mixture was allowed to stir at 0° C.-5° C. for 1 h, and then was cooled to 0° C. A solution of copper(I) chloride (55 mg, 0.4 mmol) in aq. HCl (12 N. 2 mL)) was added at 0° C. and the reaction mixture which resolved was allowed warm to rt and stir at rt for 1 h. The mixture was poured into 50 mL ice-water, extracted with ethyl acetate (3×30 mL), washed with water (2×30 mL), NaHCO3 (sat. 30 mL), brine (30 mL) and dried over Na2SO4. After removal of solvent, the residue was purified by Prep TLC with ethyl acetate/Hexane as eluent to give 45 mg (33% yield) of product P-03.

Workup

customTo a 250 mL flask which contained
temperaturethe reaction mixture which resolved was allowed warm to rt
stirringstir at rt for 1 h
extractionextracted with ethyl acetate (3×30 mL)
washwashed with water (2×30 mL), NaHCO3 (sat. 30 mL), brine (30 mL)
dry with materialdried over Na2SO4
customAfter removal of solvent
customthe residue was purified by Prep TLC with ethyl acetate/Hexane as eluent

Sources & evidence

ORD record: ord-b11de44caa2240df804b633ff445f989
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877816B2

Reaction notes

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