Methanol → Methyl 4-aminobenzenebutanoate

HRID 1508691Notes

Reaction equation

HRID 1508691 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.CO.Cl[CH2:17]Cl.C[Si](C=[N+]=[N-])(C)C>C1COCC1>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:17])=[O:12])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 270494-(4-Aminophenyl)butanoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 88628Methyl 4-aminobenzenebutanoateYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-aminophenyl)butanoic acid (180 mg, 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 4-(4-aminophenyl)butanoate as an yellowish oil (55 mg, 28% 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-1257db5af8ab487da297685776971a6f
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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