Acetic Acid → HCID 22348064, compound

HRID 897216Notes

Reaction equation

HRID 897216 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[N:9]1C=CC(C=O)=CC=1.[C:17](O)(=O)[CH3:18].C(O[BH-](O[C:31](=O)[CH3:32])OC(=O)C)(=O)C.[Na+].Cl[CH:36](Cl)[CH3:37]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH:32]=[CH:31][C:17]([CH2:18][NH2:9])=[CH:37][CH2:36]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 78124-ChloroanilineHCID 133894-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22348064HCID 22348064, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Chloroaniline (2.55 g, 20 mmol) and 4-pyridinecarboxaldehyde (1.9 mL, 20 mmol) were dissolved in dichloroethane (80 mL) prior to addition of glacial acetic acid (5 mL). The solution was stirred for 15 minutes before portionwise addition of sodium triacetoxyborohydride (4.23 g, 20 mmol). Analysis by TLC showed the reaction was complete after stirring at room temperature for 3 hours. The reaction was diluted with ethyl acetate, washed several times with 1N NaOH, and dried with sodium sulfate. Evaporation at reduced pressure gave the title amine (3.61 g). 1H NMR (300 MHz, CDCl3) δ ppm 4.27 (2H, d, J=5.89), 6.42 (2H, m), 7.02 (2H, m), 7.19 (2H, m), 8.45 (2H, m).

Workup

  1. washwashed several times with 1N NaOH
  2. dry with materialdried with sodium sulfate
  3. customEvaporation at reduced pressure

Sources & evidence

ORD record
ord-4e01b13ee4924800be770e5ffb56f076
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

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