Methanol → Methyl 4-aminobenzoate

HRID 1992234Notes

Reaction equation

HRID 1992234 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.S(Cl)(Cl)=O.N#N.[CH3:17]O>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 947NitrogenHCID 9784-Aminobenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 12082Methyl 4-aminobenzoateYield 92.1%

Procedure

2.1 g (15.6 mmol) of 4-aminobenzoic acid was dissolved in anhydrous MeOH, added 14.47 g (123.3 mmol) of thionyl chloride dropwise under N2 while stirring at rt. After dtiring for four hours, solvents were removed and redissolved in 100 mL EtOAc and 40 mL of saturated NaHCO3 aq, stirred 30 min, separated and washed with 3×20 mL water. Organics were dried yielding 2.17 g (yield 92.1%) of methyl 4-aminobenzoate. 1H NMR (300 MHz, CDCl3): 7.88 (2H, d, J=8.6 Hz), 6.66 (2H, d, J=8.6 Hz), 4.19 (2H, broad s), 3.88 (3H, s). 13C NMR (300 MHz, CDCl3): 167.8 (C═O), 151.4 (Cq), 131.9 (2×CH), 120.0 (Cq), 113.8 (2×CH), 50.9 (CH3).

Workup

  1. customsolvents were removed
  2. dissolutionredissolved in 100 mL EtOAc
  3. stirring40 mL of saturated NaHCO3 aq, stirred 30 min
  4. customseparated
  5. washwashed with 3×20 mL water
  6. customOrganics were dried

Sources & evidence

ORD record
ord-4430af02cf384aa5887093e3dae4e764
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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