Hydroxyamine hydrochloride → 2-((Hydroxyimino)methyl)-5-morpholin-4-yl-phenol

HRID 884435Notes

Reaction equation

HRID 884435 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:17][OH:18]>N1C=CC=CC=1>[OH:18][N:17]=[CH:4][C:3]1[CH:6]=[CH:7][C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:9][C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 98156592-Hydroxy-4-morpholin-4-yl-benzaldehyde

Product 1

HCID 1363488032-((Hydroxyimino)methyl)-5-morpholin-4-yl-phenolYield 35.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-hydroxy-4-morpholin-4-yl-benzaldehyde (0.135 g, 0.65 mmol) in pyridine (5 mL) was treated with hydroxylamine hydrochloride (45 mg, 0.65 mmol) and stirred for 30 min at room temperature. The reaction mixture was concentrated in vacuo and the residue was partitioned between EtOAc and 5% sodium bicarbonate. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the product as a pale yellow solid (51 mg, 35%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between EtOAc and 5% sodium bicarbonate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6bfcad2636164749b890def519cc7420
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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