Hydrochloric Acid → HCID 118869917, compound

HRID 1779126Notes

Reaction equation

HRID 1779126 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[N:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)=[C:4]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:3]=1.Cl.[N+:28]([O-])([O-])=O.[Na+].[C:33]1([NH2:43])[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][CH:34]=1.[OH-].[Na+]>CC(N(C)C)=O.O.CO.C(O)(=O)C>[NH2:43][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]([N:28]=[N:1][C:2]2[CH:7]=[CH:6][C:5]([N:8]=[N:9][C:10]3[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=3)=[C:4]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:3]=2)=[CH:35][CH:34]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 86401-NaphthylamineHCID 14798Sodium HydroxideHCID 24268Sodium NitrateHCID 118869905HCID 118869905, compound

Product 1

HCID 118869917HCID 118869917, compoundYield 79%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

7.0 g (20.0 mmol) of the 4-((4-amino-2-(octyloxy)phenyl)diazenyl)benzonitrile of Chemical Formula 1a-1 is dissolved in 200 mL of dimethyl acetamide (DMAc), 100 mL of acetic acid (AcOH), and 6.5 mL of 12 N HCl, and the resultant is maintained at 0° C. Subsequently, 1.4 g (20.3 mmol) of sodium nitrate (NaNO2) is dissolved in water, and the solution is slowly added to the reaction mixture dropwise. When the dropwise addition is complete, the reactant is maintained at 0° C. and agitated for one hour. Then, 2.9 g (20.3 mmol) of 1-naphthylamine is dissolved in methanol, the mixture is slowly dropwise added to the reaction mixture, and the mixture is agitated at 0° C. for one hour. Subsequently, the reactant is neutralized by using a sodium hydroxide (NaOH) aqueous solution to complete the reaction, and a solid precipitated therein is filtered. The mixture is purified through silica gel column chromatography (n-hexane:EtOAc=3:1), obtaining 7.9 g (15.7 mmol) of 4-((4-((4-aminonaphthalen-1-yl)diazenyl)-2-(octyloxy)phenyl)diazenyl)benzonitrile represented by the following Chemical Formula 1a-2. A yield is 79%.

Workup

  1. additionthe solution is slowly added to the reaction mixture dropwise
  2. additionWhen the dropwise addition
  3. additionthe mixture is slowly dropwise added to the reaction mixture
  4. stirringthe mixture is agitated at 0° C. for one hour
  5. customthe reaction
  6. customa solid precipitated
  7. filtrationtherein is filtered
  8. customThe mixture is purified through silica gel column chromatography (n-hexane:EtOAc=3:1)

Sources & evidence

ORD record
ord-e2edeeccf6f94220afcd0f2e04b78ab1
Source dataset
uspto-grants-2016_02
Patent number
US09268065B1

Reaction notes

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