2-[(2-Bromo-6-nitrophenyl)amino]ethanol → 2-[(2-Hydroxyethyl)amino]-3-nitrobenzonitrile

HRID 1991202Notes

Reaction equation

HRID 1991202 reaction equation
Cl[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].BrC1C=CC=C([N+]([O-])=O)C=1[NH:23][CH2:24][CH2:25][OH:26]>>[OH:26][CH2:25][CH2:24][NH:23][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 112539952-[(2-Bromo-6-nitrophenyl)amino]ethanolHCID 217860112-Chloro-3-nitrobenzonitrile

Product 1

HCID 114470952-[(2-Hydroxyethyl)amino]-3-nitrobenzonitrile

Procedure

2-[(2-hydroxyethyl)amino]-3-nitrobenzonitrile was prepared starting from 2-chloro-3-nitrobenzonitrile [prepared as described in WO 97/38983] (0.89 g) according to the procedure described for the synthesis of 2-[(2-bromo-6-nitrophenyl)amino]ethanol. Yield 1.06 g (99 %). 1H NMR (400 MHz, CD3CN) δ ppm: 3.00 (t, J=4.8 Hz, 1H), 3.68 (q, J=4.7 Hz, 2H), 3.81 (m, 2H), 6.70 (dd, J=8.6, 7.6 Hz, 1H), 7.75 (dd, J=7.6, 1.5 Hz, 1H), 8.28 (dd, J=8.6, 2.0 Hz, 1H), 8.41 (bs, 1H).

Sources & evidence

ORD record
ord-c0bbcc6f001d45b7a588bc8140ae7bc7
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

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