Hydrochloric Acid → Methyl 2-(4-amino-3-chlorophenyl)acetate

HRID 2289101

Reaction equation

HRID 2289101 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([OH:15])=[O:14])[CH:5]=[CH:6][C:7]=1[NH:8]C(=O)C.Cl.[CH3:17]O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:12][C:13]([O:15][CH3:17])=[O:14])[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 187019472-(3-Chloro-4-acetamidophenyl)acetic acid

Product 1

HCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

Procedure

A solution of 3-chloro-4-acetamidophenylacetic acid (180 grams, 0.79 moles) in methanol (2 L), was treated with concentrated HCl (200 mL) and the resulting solution refluxed for 6 hours and then stirred at room temperature for 16 hours. The mixture was concentrated in vacuo to about one-half its volume and ether (4 L) was added. The resulting precipitate was filtered, washed with ether and dried to give the title compound (173 grams) as a tan solid NMR, (CD3OD): δ 3.70 (s, 2H); 3.73 (s, 3H); 7.35 (d, 1H); 7.43 (d, 1H); 7.56 (s, 1H).

Workup

  1. temperaturethe resulting solution refluxed for 6 hours
  2. concentrationThe mixture was concentrated in vacuo to about one-half its volume and ether (4 L)
  3. additionwas added
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-2b9a8bb6879941778c593b2743c6da84
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Linked notes

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