Methanol → Methyl 2-(4-aminophenyl)acetate

HRID 1508675Notes

Reaction equation

HRID 1508675 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.CO.Cl[CH2:15]Cl.C[Si](C=[N+]=[N-])(C)C>C1COCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:15])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 145334-Aminophenylacetic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 2761030Methyl 2-(4-aminophenyl)acetateYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-aminophenyl)acetic acid (170 mg, 1.1 mmol) in a mixture of THF (4 ml), MeOH (1 ml) and dichloromethane (1 ml) in a 20-mL vial was added dropwise (trimethylsilyl)diazo-methane (1 ml, 2N in hexane) at 0° C. After the addition was complete, the resulting mixture was stirred at room temperature for 1 hr. The volatile material was removed under reduced pressure and the residue was purified by chromatography on silica gel using hexane/dichloromethane (2:1) followed by dichloromethane as eluent to give methyl 2-(4-aminophenyl)acetate as an yellowish oil (97 mg, 53% yield).

Workup

  1. additionAfter the addition
  2. customThe volatile material was removed under reduced pressure
  3. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-47ba01e5bbdc47f3b5dfc2056e06fe73
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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