Methanol → Benzoic acid, 3-amino-, methyl ester

HRID 358912Notes

Reaction equation

HRID 358912 reaction equation
[CH3:1]O.S(Cl)(Cl)=O.[NH2:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([OH:13])=[O:12]>C(Cl)(Cl)Cl.CO>[CH3:1][O:12][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][CH:16]=[C:8]([NH2:7])[CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 74193-Aminobenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 78274Benzoic acid, 3-amino-, methyl ester

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent2×

Procedure

To a chilled solution of methanol (100) was added thionyl chloride (21.25 ml, 0.29 mol). The solution was stirred for a further 30 minutes after which time m-aminobenzoic acid (10 g, 73 mmol) was added. The reaction was allowed to proceed overnight at room temperature and the solvents were then removed under reduced pressure. The product was obtained on tituration of the residue with diethyl ether. Yield 12.2 g (89%), m.p. 216°-218° C. The product was judged homogeneous by tlc in chloroform/methanol (4:1) (Rf 0.688) or chloroform/methanol (1:1) (Rf 0.597). (Found: C, 50.16; H, 5.27; N, 7.29. C8H10O2N1Cl1 requires C, 50.26; H, 5.23; N, 7.33%).

Workup

  1. additionwas added
  2. customthe solvents were then removed under reduced pressure
  3. customThe product was obtained on tituration of the residue with diethyl ether

Sources & evidence

ORD record
ord-14b3e0a64e7d449c9e5c202adcb6f6df
Source dataset
uspto-grants-1991_03
Patent number
US04997950

Reaction notes

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