Hydroxyamine hydrochloride → HCID 58531385, compound

HRID 1889694Notes

Reaction equation

HRID 1889694 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH:10]=O)=[CH:4][CH:3]=1.Cl.[NH2:18][OH:19]>CO>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)/[CH:10]=[N:18]/[OH:19])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 3085320Benzaldehyde, 3-(4-fluorophenoxy)-

Product 1

HCID 58531385HCID 58531385, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 3-(4-fluorophenoxy)benzaldehyde (3.0 g, 13.8 mmol, 1.0 eq) in methanol was added hydroxylamine hydrochloride (1.06 g, 15.2 mmol, 1.1 eq). The reaction mixture was stirred at ambient temperature for 12 h, before being concentrated in vacuo. The residue was taken in ethyl acetate and washed with water. The organic layer was dried with anhydrous Na2SO4 and concentrated to obtain the desired product (3 g, 94%). 1H NMR (400 MHz, DMSO-d6) δ 8.12 (s, 1H), 7.42-7.38 (t, 1H), 7.32-7.31 (d, 1H), 7.27-7.23 (t, 2H), 7.16 (s, 1H), 7.13-7.10 (m, 2H), 7.01-6.99 (m, 1H). MS (ESI): 232.2 (M+H)+.

Workup

  1. concentrationbefore being concentrated in vacuo
  2. washwashed with water
  3. dry with materialThe organic layer was dried with anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-80eb8cbac60c407988afafe7fc59d49c
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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