Benzaldehyde → 2-Aminopyridine

HRID 276158

Reaction equation

HRID 276158 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)(=O)C1C=CC=CC=1.C=CCCCC.C1(C)C=CC=CC=1.[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1>>[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:8])[CH2:14][CH2:15][CH2:10][CH2:11][CH2:12][CH3:13].[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1

Participants

8

Reactant 6

HCID 240BenzaldehydeHCID 243Benzoic AcidHCID 1140TolueneHCID 6115AnilineHCID 104392-AminopyridineHCID 115971-Hexene

Product 2

HCID 104392-AminopyridineHCID 74282Heptanophenone

Conditions

Temperature
130 °C

Procedure

Under the same reaction procedure and conditions as in Example 1 (benzaldehyde 0.5 mmol, aniline 0.3 mmol, bezoic acid 0.03 mmol, 1-hexene 2.5 mmol, toluene 0.87 mmol), various 2-aminopyridine derivatives 0.1 mmol as shown in the following table 3, were added to each 500 ml pressure reactor. The mixture was stirred at normal temperature for 2-3 minutes and then combined with Rh(PPh3)3Cl 0.01 mmol. While the reactor was stopped with a stopper, the reactants were heated at 130° C. for 1 hour with stirring. After completion of the reaction, gas chromatography was conducted to determine the yields of heptanophenone, products from various aminopyridine derivatives. The results are presented in Table 3, below.

Workup

  1. additionwere added to each 500 ml pressure reactor
  2. stirringwith stirring
  3. customAfter completion of the reaction, gas chromatography

Sources & evidence

ORD record
ord-fcceb4075c5c400f8b93bb53365b92fa
Source dataset
uspto-grants-2002_03
Patent number
US06353139B1

Linked notes

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