Formaldehyde → 2-(4-Chlorophenylamino)naphtho[2,3-b]furan-4,9-dione

HRID 579158

Reaction equation

HRID 579158 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[OH-].[K+].Cl[C:12]1C=CC([N+]#[C-])=C[CH:13]=1.[OH:20][C:21]1[C:22](=[O:32])[C:23]2[C:28]([C:29](=[O:31])[CH:30]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2.C=O>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:12]2[O:20][C:21]3[C:22](=[O:32])[C:23]4[C:28]([C:29](=[O:31])[C:30]=3[CH:13]=2)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 78124-ChloroanilineHCID 14797Potassium HydroxideHCID 746704-Chlorophenyl isocyanideHCID 178516607HCID 178516607, compound

Product 1

HCID 669787112-(4-Chlorophenylamino)naphtho[2,3-b]furan-4,9-dione

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

4-chlorobenzenamine 12.7 g (0.1 mol), and 470 mg BnEt3NCl was suspended in the mixture of 200 ml DCM, 200 ml CH3C1 and 200 ml 50% KOH (aq.), then was stirred at room temperature for 2 h. The organic phase was separated, washed with water (500 ml), dried with Na2SO4 and concentrated to afford yellow oil, which was purified by chromatography; 1-chloro-4-isocyanobenzene 500 mg, 2-hydroxynaphthalene-1,4-dione 635 mg (1.0 eq) and Paraformaldehyde 109 mg (1.0 eq) was dissolved in 30 ml toluene, stirred and refluxed under N2 for 4 h. After removing all solvents under reduced pressure, the residue was purified by chromatography to afford 2-(4-chlorophenylamino)naphtho[2,3-b]furan-4,9-dione as black solid. 1H NMR (300 MHz, DMSO) δ6.39 (s, 1H); 7.24˜7.29 (m, 2H); 7.41˜7.43 (dd, 2H); 7.54 (br, 1H); 7.69˜7.73 (t, 1H); 7.78˜7.82 (t, 1H); 8.13˜8.17 (t, 3H) ppm. MS-ESI: cal. 323; found: 346 (M+Na).

Workup

  1. customThe organic phase was separated
  2. washwashed with water (500 ml)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customto afford yellow oil, which
  6. customwas purified by chromatography
  7. stirringstirred
  8. temperaturerefluxed under N2 for 4 h
  9. customAfter removing all solvents under reduced pressure
  10. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-aec5d8722d4e4591839007e4e5876491
Source dataset
uspto-grants-2015_05
Patent number
US09040713B2

Linked notes

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