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

HRID 1468542Notes

Reaction equation

HRID 1468542 reaction equation
[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1)=O.CSC.B.CO>C1COCC1>[CH3:1][NH:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=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-f2fc09533dca45f28f35225a34d88b3d
Source dataset
uspto-grants-2015_04
Patent number
US09000173B2

Reaction notes

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