Methyl chloroacetate → HCID 53919154, compound

HRID 1417790Notes

Reaction equation

HRID 1417790 reaction equation
[C:1]([C:4]1[CH:13]=[C:8]([C:9]([O:11]C)=[O:10])[C:7]([OH:14])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl[CH2:16][C:17]([O:19]C)=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH2:16][C:17]([OH:19])=[O:18])=[C:8]([CH:13]=1)[C:9]([OH:11])=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 85444Methyl 5-acetylsalicylate

Product 1

HCID 53919154HCID 53919154, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1.16 g of 5-acetylsalicylic acid, methyl ester in 10 mL of N,N-dimethylformamide is added 1 g of chloroacetic acid, methyl ester and 1.2 g of potassium carbonate. After stirring this mixture at ambient temperature for 16 hours the reaction is filtered, diluted with ethyl acetate, and washed once with water and twice with brine. The ethyl acetate is dried with magnesium sulfate, filtered, and evaporated to give 5-acetyl-2-(carboxymethoxy)benzoic acid as a crude product. Crystallization from methanol at -15° C. gives 0.6 g of white crystals. 1H-NMR (CDCl3): 8.5 ppm (1H, d), 8.1 ppm (1H, dd), 6.9 ppm (1H, d), 4.8 ppm (2H, s), 4.0 ppm (3H, s), 3.8 ppm (3H, s), 2.6 ppm (3H, s). 450 mg of the above product is stirred in 1 mL of N,N-dimethylethylenediamine at ambient temperature for 16 hours. The reaction is then diluted with ethyl acetate and water. The water layer is extracted five times with ethyl acetate and the ethyl acetate from the various extractions is pooled, dried with magnesium sulfate, filtered, and evaporated to give 380 mg of 5-acetyl-2-[N-(2-dimethylaminoethyl)-3-carboxamidopropoxy]benzoic acid , methyl ester as a yellowish oil which is pure enough for further use. 1H-NMR (CDCl3): 8.6 ppm (1H, d), 8.2 ppm (1H, dd), 8.1 ppm (1H, br t), 7.0 ppm (1H, d), 4.7 ppm (2H, s), 4.0 ppm (3H, s), 3.5 ppm (2H, q), 2.7 ppm (3H, s), 2.6 ppm (2H, t), 2.3 ppm (6H, s).

Workup

  1. filtrationis filtered
  2. additiondiluted with ethyl acetate
  3. washwashed once with water and twice with brine
  4. dry with materialThe ethyl acetate is dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e4fa88808c074d54a5ee292da60a2f44
Source dataset
uspto-grants-1999_03
Patent number
US05877296

Reaction notes

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