Hydrazine → HCID 11672755, compound

HRID 595967Notes

Reaction equation

HRID 595967 reaction equation
[F:1][CH2:2][C@@H:3]([N:10]1C(=O)C2C(=CC=CC=2)C1=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.NN>CO>[F:1][CH2:2][C@H:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[NH2:10]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 118045501HCID 118045501, compound

Product 1

HCID 11672755HCID 11672755, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (S)-2-(2-fluoro-1-phenylethyl)isoindoline-1,3-dione (290 mg, 1.077 mmol) in MeOH (3.59 mL) was added hydrazine (0.507 mL, 16.15 mmol). The reaction mixture was stirred at 80° C. for 3 h. The white precipitate was filtered off. The filtrate was concentrated to yield the crude (S)-2-fluoro-1-phenylethanamine, which was used in next step without further purification. LCMS (m/z): 140.1 (MH+), 0.28 min; 1H NMR (400 MHz, CDCl3) δ ppm 7.43-7.34 (m, 4H), 7.34-7.27 (m, 1H), 4.57 (dd, J=3.7, 8.8 Hz, 1H), 4.49-4.38 (m, 1H), 4.38-4.32 (m, 1H), 4.32-4.25 (m, 1H).

Workup

  1. filtrationThe white precipitate was filtered off
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ea30fc3edb764b6cac1098e349755bcd
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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