Dinitrobenzonitrile → 2-{[2-(Benzyloxy)ethyl]amino}-6-nitrobenzonitrile

HRID 711897Notes

Reaction equation

HRID 711897 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:12]([C:15]1[CH:22]=[CH:21][CH:20]=[C:19]([N+]([O-])=O)[C:16]=1[C:17]#[N:18])([O-:14])=[O:13]>>[CH2:1]([O:8][CH2:9][CH2:10][NH:11][C:19]1[CH:20]=[CH:21][CH:22]=[C:15]([N+:12]([O-:14])=[O:13])[C:16]=1[C:17]#[N:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 520718DinitrobenzonitrileHCID 5338682-(Benzyloxy)ethanamine

Product 1

HCID 574159982-{[2-(Benzyloxy)ethyl]amino}-6-nitrobenzonitrileYield 77%

Procedure

Prepared as in Example 90c from 2-(benzyloxy)ethanamine and 2,6-dinitrobenzonitrile in 77% yield. 1H NMR (400 MHz, DMSO-d6) δ 3.49 (q, J=5.2 Hz, J=5.6 Hz, 2H), 3.59 (t, J=5.6 Hz, 2H), 4.49 (s, 2H), 6.47 (t, J=5.8 Hz, NH), 7.23-7.31 (m, 6H), 7.43 (d, J=8.0 Hz, 1H), 7.58 (t, J=8.4 Hz, 1H).

Sources & evidence

ORD record
ord-917ad38615d540e3bfcdd70f521d1938
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

Loading…