Hydrazine → 2-(2-Methoxyphenyl)propan-1-amine

HRID 2207707Notes

Reaction equation

HRID 2207707 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([CH3:22])[CH2:10][N:11]1C(=O)C2C(=CC=CC=2)C1=O.NN>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([CH3:22])[CH2:10][NH2:11]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 866996512-(2-(2-Methoxyphenyl)propyl)isoindoline-1,3-dione

Product 1

HCID 4080602-(2-Methoxyphenyl)propan-1-amineYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As shown in step 4-iv of Scheme 4, to a stirred solution of 2-(2-(2-methoxyphenyl)propyl)isoindoline-1,3-dione (363 mg, 1.23 mmol) in MeOH (4.0 mL) was added hydrazine (39.4 mg, 38.6 μL, 1.23 mmol) and the reaction was stirred for 18 hours. The precipitate that had formed was filtered, washed with MeOH, and the filtrate concentrated under reduced pressure to give 2-(methoxyphenyl)-1-propanamine as a light yellow oil (Compound 2011, 144 mg, 71% yield): 1H NMR (CDCl3) δ 7.27-7.13 (m, 2H), 6.95 (ddd, J=18.2, 12.3, 4.6 Hz, 2H), 3.84 (s, 3H), 3.39-3.18 (m, 1H), 2.86 (qd, J=12.7, 6.8 Hz, 2H), 1.44 (s, 2H), 1.24 (d, J=7.0 Hz, 3H).

Workup

  1. customThe precipitate that had formed
  2. filtrationwas filtered
  3. washwashed with MeOH
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-d51f223e0a4c42dc9783b9352bf5aad4
Source dataset
uspto-grants-2016_06
Patent number
US09376448B2

Reaction notes

Loading…