Methanol → Methyl 3-aminophenylacetate

HRID 491536

Reaction equation

HRID 491536 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 while 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) to afford methyl 3-aminophenylacetate as a brown oil. (14.1 g, 83%). 1H NMR (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-5490efe37fbc4a6b8c5795ef65309bf1
Source dataset
uspto-grants-2009_05
Patent number
US07531556B2

Linked notes

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