Methanol → Methyl 3-aminophenylacetate

HRID 2108722Notes

Reaction equation

HRID 2108722 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[CH3:16]O>>[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:16])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 571807(3-Aminophenyl)acetic acid

Product 1

HCID 13054266Methyl 3-aminophenylacetate

Conditions

Temperature
0 °C

Procedure

3-Aminophenylacetic acid (15.5 g, 0.10 mol) was suspended in methanol (150 mL) and cooled to 0° C. Thionyl chloride (11.2 mL, 0.15 mol) was added dropwise under stirring. A clear orange solution was obtained, which was stirred for 4 hours, then evaporated. The solid residue was partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate (150 mL) and the organic phase washed with saturated sodium bicarbonate (100 mL), and brine and dried (Na2SO4). Methyl 3-aminophenylacetate was isolated as a brown oil. (14.1 g, 83%). 1H NMR (500 MHz, CDCl3) δ 7.12 (1H, dd), 6.7-6.6 (3H, m), 3.71 (3H, s), 3.55 (2H, s).

Workup

  1. customA clear orange solution was obtained
  2. stirringwhich was stirred for 4 hours
  3. customevaporated
  4. customThe solid residue was partitioned between ethyl acetate (150 mL) and saturated sodium bicarbonate (150 mL)
  5. washthe organic phase washed with saturated sodium bicarbonate (100 mL), and brine
  6. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-67ea454c6d6b4d47a8ede6a4fcd9ccc3
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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