Water → Methyl 2-(acetylamino)benzoate

HRID 974412Notes

Reaction equation

HRID 974412 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([O:17][CH3:18])(=[O:16])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH2:11].C(N(CC)CC)C.O>C(Cl)Cl>[C:8]([C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[NH:11][C:1](=[O:3])[CH3:2])([O:17][CH3:18])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 8635Methyl Anthranilate

Product 1

HCID 17623Methyl 2-(acetylamino)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution consisting of 20 mL of acetic anhydride in 100 mL of methylene chloride was stirred at room temperature and 20 mL of methyl anthranilate (0.113 mole) was added dropwise over 10 min. Triethylamine (20 mL, 0.14 mole) was added and the solution was stirred at room temperature for 18 hr. An additional 100 mL of methylene chloride was added followed by 20 mL of water while cooling in an ice bath. The phases were mixed and the organic layer was separated. The aqueous layer was extracted with 20 mL of methylene chloride and the combined organic layers were dried over anhydrous sodium sulfate. Evaporation of the solvent afforded 20.05 g of product as a white solid (m.p. 96°-97° C.). 1H NMR (CDCl3) δ8.66 (d, 8.0 Hz, 1H), 8.02 (dd, 8.0 Hz, 2.0 Hz, 1H), 7.53 (dt, 8.0 Hz, 2.0 Hz, 1H), 7.03 (t, 8.0 Hz, 1H), 3.98 (s, 3H, OCH3), 2.27 (s, 3H, COCH3).

Workup

  1. stirringthe solution was stirred at room temperature for 18 hr
  2. temperaturewhile cooling in an ice bath
  3. additionThe phases were mixed
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with 20 mL of methylene chloride
  6. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-86e72a32c007421ea9ca234b5e79d587
Source dataset
uspto-grants-1991_11
Patent number
US05068392

Reaction notes

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