Water → Methyl 4-methylaminobenzoate
Reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)C.[CH:13](N(C(C)C)CC)(C)C.S(OC)(OC)(=O)=O.O>C(OCC)(=O)C>[CH3:1][O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH3:13])=[CH:7][CH:6]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
68.15 g (0.412 mol) of 4-aminobenzoic acid ethyl ester was suspended in 86 mL (0.5 mol) diisopropyl ethyl amine and 60.0 g (45 mL, 0.474 mol) dimethyl sulfate was added drop wise. During the addition, the temperature rose to 95° C. The reaction is allowed to continue for 1 hour at 120° C. The reaction mixture was allowed to cool down to room temperature and 300 mL of water was added. The mixture was allowed to stand over night. The precipitated residue was isolated and treated with 250 mL of ethyl acetate. The solution in ethyl acetate was extracted twice with 100 mL of water, dried over MgSO4 and evaporated under reduced pressure. 4-methylaminobenzoic acid ethyl ester was purified by preparative column chromatography on Kieselgel 60 (Aldrich), using cyclohexane/ethyl acetate 4/1 as eluent. 36.3 g 4-methylaminobenzoic acid methyl ester was isolated (m.p. 66-67° C.).
Workup
- additionDuring the addition
- customrose to 95° C
- waitto stand over night
- customThe precipitated residue was isolated
- extractionThe solution in ethyl acetate was extracted twice with 100 mL of water
- dry with materialdried over MgSO4
- customevaporated under reduced pressure
- custom4-methylaminobenzoic acid ethyl ester was purified by preparative column chromatography on Kieselgel 60 (Aldrich)
Sources & evidence
- ORD record
- ord-aa6292919aa2425fbcf9d5e3b84f2db8
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344038B2
Reaction notes
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