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

HRID 2088777Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([CH:25]([O:28][CH3:29])[O:26][CH3:27])[CH:17]=1.O>CC(N(C)C)=O>[CH3:29][O:28][CH:25]([O:26][CH3:27])[C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[N+:22]([O-:24])=[O:23])[O:8][C:4]1[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3-Aminophenol (0.050 mol) was dissolved in DMA (100 mL). K2CO3 (0.060 mol) was added. 4-Chloro-2-dimethoxymethyl-1-nitrobenzene (0.050 mol) was added, and the reaction mixture was stirred overnight at 100° C. and then for 2 hours at 120° C. The reaction mixture was poured into water and this mixture was extracted with diisopropyl ether. The separated organic layer was dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2:CH3OH 100:0 (to remove unreacted 4-chloro-2-dimethoxymethyl-1-nitrobenzene) up to 70:30). The desired fractions were collected and the solvent was evaporated to yield a residue.

Workup

waitfor 2 hours at 120° C
extractionthis mixture was extracted with diisopropyl ether
customThe separated organic layer was dried
filtrationfiltered
customthe solvent evaporated
customThe residue was purified by column chromatography over silica gel (eluent
customThe desired fractions were collected
customthe solvent was evaporated
customto yield a residue

Sources & evidence

ORD record: ord-bf96762f99ff4766a151e8daf80e9d05
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436006B2

Reaction notes

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