Sodium Iodide → 3-(Boc-aminoethyloxy)benzonitrile

HRID 747656Notes

Reaction equation

[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9]Br)([CH3:4])([CH3:3])[CH3:2].[OH:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:7][CH2:8][CH2:9][O:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[C:16]#[N:17])=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

5.85 g (29 mmol) of t-butyl(2-bromoethyl)carbamate was dissolved in 100 ml of dimethylformamide. 2.38 g (26.4 mmol) of 3-hydroxybenzonitrile, 3.04 g (53 mmol) of potassium carbonate and 4.31 g (53 mmol) of sodium iodide were added to the solution, and the obtained mixture was stirred at 50° C. for 6 hours. After the treatment with ethyl acetate as the extractant in an ordinary manner, the crude product was obtained. After the purification by silica gel column chromatography, the title compound was obtained.

Workup

customAfter the purification by silica gel column chromatography

Sources & evidence

ORD record: ord-cfe03c38b4024dc18bfe0d4ce8fb5aab
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396844B1

Reaction notes

Loading…