Hydroxylamine → HCID 72806160, compound

HRID 354239Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:21][OH:22].[OH-].[Na+].CO>O>[F:1][C:2]1[CH:3]=[C:4]([C:8](=[N:21][OH:22])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A reaction vessel was charged with 1-(3-fluorophenyl)-2-(5-trifluoromethyl-2-pyridinyl)ethanone (2 g, 7 mmol), hydroxylamine (2.2 g, 32 mmol), 10% NaOH aqueous solution (11 ml, 27 mmol) and methanol (24 ml). The reaction mixture was heated to 70° C. and stirred at 70° C. for 3 hrs. It was then cooled to room temperature and water (12 ml) was added. The mixture was stirred at 0° C. for 1 hr. The solids were collected on a filter, washed with water, and dried under vacuum at 50° C. overnight to provide 1.9 g (91%) of the title compound as a solid with purity 99% AUC by HPLC (Phenomenex Luna 3μ cyano, 100 mm×4.6 mm. Flow rate: 1 ml/min. UV detection: 220 nm. Eluent: 75% A, 25% B. A: 80/20/0.05 water/acetonitrile/TFA. B: 20/80/0.05 water/acetonitrile/TFA).

Workup

temperatureIt was then cooled to room temperature
stirringThe mixture was stirred at 0° C. for 1 hr
customThe solids were collected on a filter
washwashed with water
customdried under vacuum at 50° C. overnight

Sources & evidence

ORD record: ord-a68f2c02654c40518672bc02054c98b6
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06756498B2

Reaction notes

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