Hydrochloric Acid → HCID 131732718, compound

HRID 1470528Notes

Reaction equation

HRID 1470528 reaction equation
CC(C1C=CC(OC)=C(OC)C=1)=O.COC1C=CC(NC2N=CC=CC=2C=O)=CC=1.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([NH:39][C:40]2[C:45]([CH:46]=[CH:47][C:48]([C:50]3[CH:55]=[C:54](OC)[C:53]([O:58][CH3:59])=[C:52]([O:60][CH3:61])[CH:51]=3)=[O:49])=[CH:44][CH:43]=[CH:42][N:41]=2)=[CH:35][CH:34]=1.Cl>CO>[CH3:61][O:60][C:52]1[CH:51]=[C:50]([C:48](=[O:49])[CH:47]=[CH:46][C:45]2[C:40]([NH:39][C:36]3[CH:35]=[CH:34][C:33]([O:32][CH3:31])=[CH:38][CH:37]=3)=[N:41][CH:42]=[CH:43][CH:44]=2)[CH:55]=[CH:54][C:53]=1[O:58][CH3:59]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 143283,4-Dimethoxyphenyl methyl ketoneHCID 22917748HCID 22917748, compoundHCID 131732719HCID 131732719, compound

Product 1

HCID 131732718HCID 131732718, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,4-dimethoxyacetophenone (78.90 mg, 0.438 mmol) in methanol (5 mL) was added 2N Ba(OH)2 solution (2 mL) and stirred for 5 minutes. Then added 2-(4-methoxyphenylamino) nicotinaldehyde (100 mg, 0.438 mmol) and the reaction mixture was stirred at a temperature of 30° C. for 6h and the reaction was monitored by TLC. After 8h the reaction mixture was acidified with 2N HCl. The resulting precipitate was filtered, washed thoroughly with water and dried over anhydrous CaCl2. The precipitate was recrystallized using ethanol to obtain pure (6i) (150.8 mg, 88% yield).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed thoroughly with water
  3. dry with materialdried over anhydrous CaCl2
  4. customThe precipitate was recrystallized

Sources & evidence

ORD record
ord-26f8b83a4be745bc9413577aca507e0e
Source dataset
uspto-grants-2015_04
Patent number
US09006451B1

Reaction notes

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