Methyl 4-acetylbenzoate → HCID 73652604, compound

HRID 1049091Notes

Reaction equation

HRID 1049091 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH3:11])=[CH:6][CH:5]=1.Cl.[NH2:15][OH:16].C([O-])(=O)C.[Na+]>CO>[OH:16][N:15]=[C:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([O:2][CH3:1])=[O:13])=[CH:5][CH:6]=1)[CH3:11]

Participants

5

Reactant 3

HCID 137990Methyl 4-acetylbenzoateHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 73652604HCID 73652604, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-acetylbenzoic acid methyl ester (1.0 g, 5.6 mmol), hydroxylamine hydrochloride (3.1 g, 45 mmol) and sodium acetate (3.7 g, 45 mmol) in methanol (50 mL) was heated at 40° C. for 2 hours. The mixture was evaporated to dryness and the residue partitioned between EtOAc (40 mL) and water (40 mL). The organic layer was washed with brine (40 mL), dried over anhydrous MgSO4 and evaporated to dryness to afford the title compound as a white solid (1.04 g, 96%). LC-MS: (FA) ES+ 194; 1H NMR (400 MHz, MeOD) δ 8.02-7.98 (m, 2H), 7.78-7.75 (m, 2H), 3.90 (s, 3H), 2.24 (s, 3H).

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue partitioned between EtOAc (40 mL) and water (40 mL)
  3. washThe organic layer was washed with brine (40 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-4f79006d7a464fb093ef971935e96c26
Source dataset
uspto-grants-2016_07
Patent number
US09382197B2

Reaction notes

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