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

HRID 929536Notes

Reaction equation

HRID 929536 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-ca2cdb2e8f284da8bb919cc0c9e5e1ce
Source dataset
uspto-grants-2016_03
Patent number
US09296701B2

Reaction notes

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