Hydrochloric Acid → HCID 71254826, compound

HRID 1508341Notes

Reaction equation

HRID 1508341 reaction equation
[Cl:1][C:2]1[C:3]([F:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)/[CH:5]=[N:6]/[OH:7].ClC1C(F)=[C:15]([CH:18]=[CH:19]C=1)[CH:16]=[O:17].Cl.N[OH:24].[OH-].[Na+].Cl>CCO.O>[Cl:1][C:2]1[C:3]([F:11])=[C:4]([C:5]2[C:18]([CH3:19])=[C:15]([C:16]([OH:24])=[O:17])[O:7][N:6]=2)[CH:8]=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 7363353-Chloro-2-fluorobenzaldehydeHCID 56776464HCID 56776464, compound

Product 1

HCID 71254826HCID 71254826, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(E)-3-Chloro-2-fluorobenzaldehyde oxime: To the solution of 3-chloro-2-fluorobenzaldehyde (1.3 g, 8.20 mmol) and hydroxylamine hydrochloride (0.695 g, 10.00 mmol) in EtOH (6.83 mL)/water (6.83 mL) was added 1 N NaOH (10.00 mL, 10.00 mmol). The reaction was stirred at rt for 4 h, then it was acidified to pH 6 with 1 N HCl which gave a white suspension. The reaction mixture was filtered, and the solid was rinsed with water, and air-dried to afford the desired product (1.31 g, 92%) as a white solid. MS(ESI) m/z: 174.0 (M+H)+. 1H NMR (500 MHz, CDCl3) δ 8.36 (s, 1H), 7.74 (s, 1H), 7.66 (ddd, J=7.8, 6.3, 1.7 Hz, 1H), 7.42 (ddd, J=8.0, 7.2, 1.7 Hz, 1H), 7.13-7.07 (m, 1H) ppm.

Workup

  1. customgave a white suspension
  2. filtrationThe reaction mixture was filtered
  3. washthe solid was rinsed with water
  4. customair-dried

Sources & evidence

ORD record
ord-238e61cde72249ca8e5c00b9133e95ca
Source dataset
uspto-grants-2015_12
Patent number
US09221818B2

Reaction notes

Loading…