Methanol → Methyl 2-(4-(methylamino)phenyl)acetate

HRID 1055350Notes

Reaction equation

HRID 1055350 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH:12]=O)=[CH:7][CH:6]=1.CSC.B.CO>C1COCC1>[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH3:12])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 86634878HCID 86634878, compound

Product 1

HCID 15892780Methyl 2-(4-(methylamino)phenyl)acetateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl(4-formylaminophenyl)acetate (4.31 g) in THF (20.0 mL) at 0° C. was slowly added borane dimethylsulfide (8.61 mL, 90.8 mmol). The reaction mixture was stirred at room temperature overnight and then cooled to 0° C. MeOH (15 mL) was added cautiously and the resulting mixture was stirred for 3 h. The mixture was then concentrated under reduced pressure to give the title compound (4.0 g, 73% yield, 2 steps) as a clear oil.

Workup

  1. customat 0° C.
  2. temperaturecooled to 0° C
  3. stirringthe resulting mixture was stirred for 3 h
  4. concentrationThe mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-5e8f8fc836364d01ad66a877742a6f1a
Source dataset
uspto-grants-2016_07
Patent number
US09394275B2

Reaction notes

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