Acetyl chloride → HCID 54429507, compound

HRID 2051241Notes

Reaction equation

HRID 2051241 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][O:6][C:7](=[O:26])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([NH:23][OH:24])[CH3:22])[C:16]=1[Cl:25].C([O-])(=O)C.[Na+].O1CCOCC1>O>[CH3:5][O:6][C:7](=[O:26])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([N:23]([C:1](=[O:3])[CH3:2])[OH:24])[CH3:22])[C:16]=1[Cl:25]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 312751,4-DioxaneHCID 517045Sodium AcetateHCID 53964896HCID 53964896, compound

Product 1

HCID 54429507HCID 54429507, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Acetyl chloride (0.49 g, 6.2 mmol) is added dropwise to a mixture of 2[[2-chloro-3-[1-(N-hydroxyamino)ethyl]phenyl]amino]benzoic acid methyl ester (2.0 g, 6.2 mmol) and sodium acetate (0.77 g, 9.4 mmol) in 2:1 dioxane:water with ice bath cooling. The reaction mixture is stirred at room temperature overnight. It is then diluted with water (100 mL) and extracted with ethyl acetate (200 mL). The organic layer is washed with water (200 mL) and brine (100 mL), and is dried over magnesium sulfate. Evaporation of the ethyl acetate gives the crude product which is purified by flash chromatography (silica, 50% ethyl acetate/hexane). Recrystallization gives 2-[[3-[1-(acetylhydroxyamino)ethyl]-2-chlorophenyl]amino]benzoic acid methyl ester (0.34 g, 15%). mp=171-172° C.

Workup

  1. extractionextracted with ethyl acetate (200 mL)
  2. washThe organic layer is washed with water (200 mL) and brine (100 mL)
  3. dry with materialis dried over magnesium sulfate
  4. customEvaporation of the ethyl acetate
  5. customgives the crude product which
  6. customis purified by flash chromatography (silica, 50% ethyl acetate/hexane)
  7. customRecrystallization

Sources & evidence

ORD record
ord-9ee4896da49b43459e8fe155bc968780
Source dataset
uspto-grants-1991_05
Patent number
US05017604

Reaction notes

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