Hydrochloric Acid → HCID 131732721, compound

HRID 1470530Notes

Reaction equation

HRID 1470530 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[C:6]([O:14][CH3:15])[CH:5]=1)=[O:3].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([NH:28][C:29]2[N:36]=[CH:35][CH:34]=[CH:33][C:30]=2[CH:31]=O)[CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25].COC1C=CC(NC2C(C=CC(C3C=C(OC)C(OC)=C(OC)C=3)=O)=CC=CN=2)=CC=1.Cl>CO>[CH3:15][O:14][C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH:1]=[CH:31][C:30]2[C:29]([NH:28][C:20]3[CH:21]=[C:22]([O:26][CH3:27])[C:23]([O:24][CH3:25])=[C:18]([O:17][CH3:16])[CH:19]=3)=[N:36][CH:35]=[CH:34][CH:33]=2)[CH:9]=[C:8]([O:10][CH3:11])[C:7]=1[O:12][CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 143453',4',5'-TrimethoxyacetophenoneHCID 21284351HCID 21284351, compoundHCID 131732719HCID 131732719, compound

Product 1

HCID 131732721HCID 131732721, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,4,5-trimethoxyacetophenone (145 mg, 0.693 mmol) in methanol (5 mL) was added 2N Ba(OH)2 solution (2 ml) and stirred for 5 minutes. Then added 2-(3,4,5-trimethoxyphenylamino)nicotinaldehyde (200 mg, 0.693 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 is 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 (6v) (289 mg, 87% 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-9e735e55b4a5460e9d34d5ba4b447ea0
Source dataset
uspto-grants-2015_04
Patent number
US09006451B1

Reaction notes

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