Hydroxyamine hydrochloride → 6-phenoxy-2H-1-benzopyran-3-carboxaldehyde oxime

HRID 466191Notes

Reaction equation

HRID 466191 reaction equation
[O:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][C:14]([CH:17]=O)=[CH:13][C:12]=2[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:21][OH:22]>N1C=CC=CC=1.C(O)C>[O:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][C:14]([CH:17]=[N:21][OH:22])=[CH:13][C:12]=2[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 149712656-phenoxy-2H-1-benzopyran-3-carboxaldehyde

Product 1

HCID 856778336-phenoxy-2H-1-benzopyran-3-carboxaldehyde oxime

Reagents, catalysts & solvents 1

HCID 21975839Pyridine ethanolSolvent

Procedure

6-Phenoxy-2H-1-benzopyran-3-carboxaldehyde (5.00 g, 19.9 mmol) is dissolved in 175 ml of pyridine/ethanol (1:1) and treated with hydroxylamine hydrochloride (2.07 g, 29.7 mmol). The mixture is stirred for 1 hour and partitioned between ether and water. The aqueous layer is extracted with ether, and the ether layer is washed with 2N HCl, dried (MgSO4) and evaporated to give 6-phenoxy-2H-1-benzopyran-3-carboxaldehyde oxime as a pale yellow solid.

Workup

  1. custompartitioned between ether and water
  2. extractionThe aqueous layer is extracted with ether
  3. washthe ether layer is washed with 2N HCl
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-8e53bd09a0ed4cb3af88766be1a44130
Source dataset
uspto-grants-1992_10
Patent number
US05155130

Reaction notes

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