2-Chloro-4-methoxy-1-nitrobenzene → 1-Diethylamino-3-(5'-methoxy-2'-nitro-phenoxy)-naphthalene

HRID 329166Notes

Reaction equation

HRID 329166 reaction equation
O1C=CC=CN=N1.Cl[C:9]1[CH:10]=[C:11]([O:18][CH3:19])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16].[CH2:20]([N:22]([CH2:34][CH3:35])[C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]([OH:33])[CH:24]=1)[CH3:21]>>[CH2:34]([N:22]([CH2:20][CH3:21])[C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]([O:33][C:9]2[CH:10]=[C:11]([O:18][CH3:19])[CH:12]=[CH:13][C:14]=2[N+:15]([O-:17])=[O:16])[CH:24]=1)[CH3:35]

Participants

4

Reactant 3

HCID 5937892-Chloro-4-methoxy-1-nitrobenzeneHCID 158689364-(Diethylamino)naphthalen-2-olHCID 21866441Oxadiazepine

Product 1

HCID 214388631-Diethylamino-3-(5'-methoxy-2'-nitro-phenoxy)-naphthalene

Procedure

Thus, for example, a compound of the formula ##STR16## is obtained by reaction of 2-chloro-3-nitro-pyridine with 3-diethylaminothiophenol to give 2(3'-diethylaminothiophenoxy)-3-nitro-pyridine, reduction to the 3-amino compound, diazotisation and intramolecular coupling. The oxadiazepine derivative ##STR17## is obtained, for example, by reaction of 3-chloro-4-nitroanisole with 1-diethylamino-3-hydroxynaphthalene to give 1-diethylamino-3-(5'-methoxy-2'-nitro-phenoxy)-naphthalene, reduction to the 2'-amino compound, diazotisation and internal coupling.

Sources & evidence

ORD record
ord-364b9b4924e84f80b3bd4024e8367219
Source dataset
uspto-grants-1977_04
Patent number
US04020063

Reaction notes

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