Water → Methyl 2-[(chloroacetyl)amino]benzoate

HRID 1381183Notes

Reaction equation

HRID 1381183 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(=O)([O-])[O-].[K+].[K+].[Cl:18][CH2:19][C:20](Cl)=[O:21].O>CC(C)=O.O>[Cl:18][CH2:19][C:20]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8635Methyl AnthranilateHCID 11430Potassium Carbonate

Product 1

HCID 295954Methyl 2-[(chloroacetyl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

38 Grams of methyl anthranilate and 35 g of potassium carbonate were dissolved in 300 ml of a mixture of acetone-water (2:1), then to this solution was added dropwise 30 g of chloroacetyl chloride under an ice-cooled condition with stirring. After completion of the addition, the reaction was carried out at a room temperature for 2 hours, then 200 ml of water was added to the reaction mixture, and the mixture obtained was ice-cooled, and the crystals precipitated were collected by filtration. The crystals collected were washed with water and ethanol, and recrystallized from methanol to obtain 48.6 g of methyl o-(α-chloroacetylamino)benzoate in the form of colorless needle-like crystals. Melting point: 97°-99° C.

Workup

  1. temperaturecooled condition
  2. additionAfter completion of the addition
  3. customthe mixture obtained
  4. temperaturecooled
  5. customthe crystals precipitated
  6. filtrationwere collected by filtration
  7. customThe crystals collected
  8. washwere washed with water and ethanol
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-9390966a078a435b88c8b3049d6b86b1
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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