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Water → 3-Amino-4-[4-(3-Pyridyl)Anilino]-3-Cyclobutene-1,2-Dione

HRID 322060
Notes
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Reaction equation

HRID 322060 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[NH2:14][C:15]1[C:16](=[O:23])[C:17](=[O:22])[C:18]=1OCC.O>N1C=CC=CC=1>[NH2:14][C:15]1[C:16](=[O:23])[C:17](=[O:22])[C:18]=1[NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 4595224-(Pyridin-3-yl)anilineHCID 151463363-Amino-4-ethoxycyclobut-3-ene-1,2-dione

Product 1

HCID 98167573-Amino-4-[4-(3-Pyridyl)Anilino]-3-Cyclobutene-1,2-DioneYield 41.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-(4-aminophenyl)pyridine (0.51 g) and 3-amino-4-ethoxy-3-cyclobutene 1,2-dione (0.42 g) in pyridine (2 ml) is stirred at 80° for 20 hours. The cool mixture is treated with water (15 ml), and the solid filtered off and washed with water and hot methanol. Recrystallation from dimethylformamide gives 0.33 g of the title compound, mp 3224° C. dec.

Workup

  1. filtrationthe solid filtered off
  2. washwashed with water and hot methanol

Sources & evidence

ORD record
ord-aa05ba3bd85e44dba5f6ce3a32446e72
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211220B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes