Methanol → Methyl 4-(2-aminophenyl)butanoate

HRID 1485947Notes

Reaction equation

HRID 1485947 reaction equation
[NH:1]1[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[CH3:13][OH:14]>S(=O)(=O)(O)O>[CH3:13][O:14][C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[NH2:1]

Participants

4

Reactant 2

HCID 887MethanolHCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-one

Product 1

HCID 237256Methyl 4-(2-aminophenyl)butanoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
70 °C

Procedure

To 1,3,4,5-tetrahydro-benzo[b]azepin-2-one (1 g, 6.2 mmol) in MeOH (8 mL), concentrated sulfuric acid (0.5 mL) was added and the mixture was stirred at room temperature for 2 hrs and at 70° C. for an additional hr. The solvent was removed and DCM and water were added. The organic layer was removed and the aqueous layer was basified with sat NaHCO3 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated in vacuo to yield 4-(2-amino-phenyl)-butyric acid methyl ester (0.93 g). MS [M+H]+: 194.1; tR=1.49 min. (method 1)

Workup

  1. customThe solvent was removed
  2. additionDCM and water were added
  3. customThe organic layer was removed
  4. extractionextracted with EtOAc (3×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3569ab0526844299ba3508334e1f4d4d
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

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