Hydrochloric Acid → HCID 59187024, compound

HRID 1887248Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1.[OH-:16].[Na+].Cl>CO>[O:9]([CH2:8][C:6]1[CH:5]=[CH:4][NH:3][C:2](=[O:16])[CH:7]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 170 °C

Procedure

To a solution of 2-chloro-4-(phenoxymethyl)pyridine (2.34 g, 10.68 mmol) in anhydrous methanol (30 mL) in a steel bomb was added sodium hydroxide (3.20 g, 80.11 mmol). The reaction mixture was stirred at 170° C. for 16 hours, cooled to 0° C. and neutralized with cold concentrated hydrochloric acid, followed by the addition of methanol (10 mL) and filtration. The filtrate was concentrated in vacuo and the residue was washed with methanol and hexane. The title compound was obtained as a colorless solid in 93% (2 g): 1H NMR (300 MHz, CDCl3) δ 13.00 (br s, 1H), 7.35-7.25 (m, 3H), 6.99-6.90 (m, 3H), 6.64 (s, 1H), 6.34 (d, J=6.6 Hz, 1H), 4.93 (s, 2H); MS (ES+) m/z 202.2 (M+1).

Workup

concentrationThe filtrate was concentrated in vacuo
washthe residue was washed with methanol and hexane

Sources & evidence

ORD record: ord-7c6cfa924afb4499bfac3dde2719e381
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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