Hydrochloric Acid → HCID 14941567, compound

HRID 1463670Notes

Reaction equation

HRID 1463670 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2([CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[C:20]3[CH:19]=[C:18]([N+:21]([O-])=O)[CH:17]=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:3][CH:2]=1.Cl.[OH-].[K+]>C(O)C.O.[Fe].[OH-].[Fe+2].[OH-]>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]2([CH2:24][C:25]3[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=3)[C:20]3[CH:19]=[C:18]([NH2:21])[CH:17]=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 15296106HCID 15296106, compound

Product 1

HCID 14941567HCID 14941567, compoundYield 82.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 10129897Iron hydroxide (Fe(OH)2)CatalystHCID 19096565Water ethanolSolvent

Procedure

1.68 g (4.27 mmole) of 9,9-bis(4-pyridinylmethyl)-2-nitrofluorene was suspended in 5 ml of ethanol/water (1:1) and 1.43 g of powdered iron was added. The mixture was heated to boiling and 0.3 ml conc. hydrochloric acid was added dropwise. After completion of addition, the mixture was refluxed 2 hrs. The cooled mixture was basified with KOH, iron hydroxide filtered off and the filtrate evaporated. The residue was dissolved in ether-CH2Cl2 (3:1), washed with water, saturated sodium chloride, dried (MgSO4) and evaporated to yield 1.28 g of the title product. NMR (CDCl3, 200 MHz) δ: 3.33(s,4H), 6.53(dd,4H), 6.60(d,J=2.0 Hz,1H), 6.79(d,J=2.0 Hz,1H), 7.18(d,4H), 7.37(dd,1H), 8.11(dd,4H), m.p. (trihydrochloride) >300°. HRMS calculated for C25H21N3 : 363.1735 Found: 363.1728.

Workup

  1. additionwas added dropwise
  2. additionAfter completion of addition
  3. temperaturethe mixture was refluxed 2 hrs
  4. filtrationfiltered off
  5. customthe filtrate evaporated
  6. dissolutionThe residue was dissolved in ether-CH2Cl2 (3:1)
  7. washwashed with water, saturated sodium chloride
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-cc8d8f095c3741da8eca19ab0e965ca6
Source dataset
uspto-grants-1994_04
Patent number
US05300642

Reaction notes

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