Water → 3-(3-Dimethoxymethyl-4-nitro-phenoxy)phenylamine

HRID 1968824Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([CH:17]([O:20][CH3:21])[O:18][CH3:19])[CH:9]=1.[NH2:22][C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=1.O>CC(N(C)C)=O>[CH3:19][O:18][CH:17]([O:20][CH3:21])[C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][C:11]=1[N+:14]([O-:16])=[O:15])[O:29][C:25]1[CH:24]=[C:23]([NH2:22])[CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 130 °C

Procedure

K2CO3 (0.17 mol) and then 4-chloro-2-dimethoxymethyl-1-nitro-benzene (0.1 mol) was added to a solution of 3-amino-phenol (0.15 mol) in DMA (200 mL) and the reaction mixture was stirred at 130° C. for 24 hours. The mixture was poured out into water and extracted with diisopropyl ether. The extract was purified by column chromatography over silica gel (eluent: CH2Cl2:CH3OH 100:0 to 65:35). The product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

extractionextracted with diisopropyl ether
customThe extract was purified by column chromatography over silica gel (eluent: CH2Cl2:CH3OH 100:0 to 65:35)
customThe product fractions were collected
customthe solvent was evaporated

Sources & evidence

ORD record: ord-39b87a7da28242a5ab1b4fb564b80742
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426429B2

Reaction notes

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