Ethanol → HCID 136347709, compound

HRID 2306660Notes

Reaction equation

HRID 2306660 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[OH:14])(=O)[CH3:2].CCO.Cl.[NH2:19][OH:20]>[OH-].[Na+]>[OH:14][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:4]=1[C:1](=[N:19][OH:20])[CH3:2])[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 22610067Methyl 4-acetyl-3-hydroxybenzoate

Product 1

HCID 136347709HCID 136347709, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Methyl 4-acetyl-3-hydroxybenzoate (350 mg, 1.8 mmole) is combined with 5 ml absolute EtOH. The solution is treated with hydroxylamine hydrochloride (125 mg, 1.8 mmole) dissolved in 0.9 ml 2N aqueous NaOH, and the reaction is stirred overnight at rt. The volatiles are removed in vacuo and the residue is washed with H2O, collected, and dried to give 294 mg (78%) of methyl 3-hydroxy-4-[N-hydroxyethanimidoyl]benzoate as a tan solid. MS (EI) m/z: 209 (M+).

Workup

  1. customThe volatiles are removed in vacuo
  2. washthe residue is washed with H2O
  3. customcollected
  4. customdried

Sources & evidence

ORD record
ord-21289b0afe6342acbdf4645abada056c
Source dataset
uspto-grants-2004_12
Patent number
US06828330B2

Reaction notes

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