Morpholine → HCID 67508051, compound

HRID 1431715Notes

Reaction equation

[NH2:1][C:2]1[C:9]([I:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4](Cl)[CH:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>>[NH2:1][C:2]1[C:9]([I:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:3]=1

Participants

Reactant 2

HCID 8083Morpholine

HCID 109128704-amino-2-chloro-5-iodobenzonitrile

Product 1

HCID 67508051HCID 67508051, compound

Conditions

Temperature: 200 °C

Procedure

4-Amino-2-chloro-5-iodobenzonitrile (0.60 g, 2.1 mmol) and morpholine (2.0 mL, 23 mmol) were added to a microwave vial and heated in the microwave to 200° C. After 60 minutes, the residue was concd then purified on silica gel (0-40% EtOAc in hexanes) to yield a white solid as 4-amino-5-iodo-2-morpholinobenzonitrile. Mass Spectrum (pos.) m/e: 330.0 (M+H)+. 4-amino-2-morpholinobenzonitrile was also isolated. 1H NMR (500 MHz, CDCl3) δ ppm 7.35 (1H, d, J=8.3 Hz), 6.28 (1H, dd, J=8.4, 2.1 Hz), 6.20 (1H, d, J=2.0 Hz), 4.14 (2H, br. s.), 3.95 (4H, m), 3.24 (4H, m). Mass Spectrum (pos.) m/e: 204.1 (M+H)+.

Workup

customthe residue was concd then purified on silica gel (0-40% EtOAc in hexanes)

Sources & evidence

ORD record: ord-7578c4bba76043598185c921ad2ffecb
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940724B2

Reaction notes

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