Acetyl chloride → N-[4-Methoxy-3-(methoxycarbonyl)phenyl]ethanimidic acid

HRID 323453Notes

Reaction equation

HRID 323453 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C(N(CC)C(C)C)(C)C.[C:23](Cl)(=[O:25])[CH3:24].CO.ClCCl>ClCCl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([NH:13][C:23](=[O:25])[CH3:24])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 89843Methyl 5-amino-o-anisateHCID 21226129Dichloromethane methanol

Product 1

HCID 4153338N-[4-Methoxy-3-(methoxycarbonyl)phenyl]ethanimidic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Alternately, combine methyl 2-methoxy-5-aminobenzoate (1.5 g, 8.3 mmol) and dichloromethane (25 mL). Cool in an ice bath. Add N,N-diisopropylethylamine (3.2 mL, 18.2 mmol), and acetyl chloride (0.62 mL, 9.7 mmol). Warm to ambient temperature. After 4 hours, dilute the reaction mixture with dichloromethane and extract three times with half saturated aqueous ammonium chloride solution. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 3% methanol/dichloromethane/0.1% concentrated aqueous ammonia to give methyl 2-methoxy-5-acetamidobenzoate: mp; 132-134° C. Elemental Analysis calculated for C11H13NO4: C, 59.19; H, 5.87. Found C, 59.04; H, 5.86.

Workup

  1. temperatureCool in an ice bath
  2. extractionextract three times with half saturated aqueous ammonium chloride solution
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue

Sources & evidence

ORD record
ord-18a375fb38c74b72bd73de1182f1a24b
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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