Formic Acid → HCID 66883578, compound

HRID 1760356Notes

Reaction equation

HRID 1760356 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=[O:12])C)[N:5]=1)(=O)C.C[C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH2:16].C(O)=O>CO.O1CCCC1>[NH2:5][C:6]1[C:10](=[O:12])[C:4]2[C:9](=[CH:8][CH:7]=1)[C:19]1[C:18](=[CH:17][C:15]([NH2:16])=[CH:14][CH:20]=1)[CH:1]=2

Participants

6

Reactant 3

HCID 284Formic AcidHCID 7242O-ToluidineHCID 707902,6-Diacetylpyridine

Product 1

HCID 66883578HCID 66883578, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

100 ml of methanol, 6.53 g of 2,6-diacetylpyridine (molecular weight 163.18; 40 mmols) and 21.4 g of 2-methylaniline (molecular weight 107.15; 200 mmols) were put into a 300 ml flask, and thoroughly stirred to prepare a homogeneous mixture. 0.6 ml of formic acid was added to this, and further the mixture was stirred at room temperature for 4 hours to make the compounds reacted completely. The resulting yellow crystal was taken out through filtration, washed with methanol, and dried under reduced pressure to obtain 10.3 g of 2,6-diacetylpyridine-di(2-methylphenyl)imine (molecular weight 341.45; 30.3 mmols, yield 76%) Next, 10 ml of tetrahydrofuran, 20 ml of methanol, 5.1 g (15 mmols) of 2,6-diacetylpyridine-di(2-methylphenyl)imine and 1.96 g of 2,7-diaminofluorenone (molecular weight 196.25; 10 mmols) were put into a 100 ml flask, and thoroughly stirred to prepare a homogeneous mixture. 0.6 ml of formic acid was added to this, and further the mixture was stirred at room temperature for 4 hours to make the compounds reacted completely. The resulting yellow crystal was taken out through filtration, washed with methanol, and dried under reduced pressure. Its NMR spectrum was assigned as the intended ligand (molecular weight 664.84; 2.65 g, 4.0 mmols, yield 53%).

Workup

  1. customto prepare a homogeneous mixture
  2. stirringwas stirred at room temperature for 4 hours
  3. customreacted completely
  4. filtrationThe resulting yellow crystal was taken out through filtration
  5. washwashed with methanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-ab14cef0e29042b39bb6aff7624d2326
Source dataset
uspto-grants-2005_01
Patent number
US06841693B1

Reaction notes

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