Hydrochloric Acid → HCID 131732723, compound

HRID 1470532Notes

Reaction equation

HRID 1470532 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)=[O:3].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH:24][C:25]2[N:32]=[CH:31][CH:30]=[CH:29][C:26]=2[CH:27]=O)[CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21].COC1C=CC(NC2C(C=CC(C3C=C(OC)C(OC)=C(OC)C=3)=O)=CC=CN=2)=CC=1.Cl>CO>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH:1]=[CH:27][C:26]2[C:25]([NH:24][C:16]3[CH:17]=[C:18]([O:22][CH3:23])[C:19]([O:20][CH3:21])=[C:14]([O:13][CH3:12])[CH:15]=3)=[N:32][CH:31]=[CH:30][CH:29]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 74764'-MethoxyacetophenoneHCID 21284351HCID 21284351, compoundHCID 131732719HCID 131732719, compound

Product 1

HCID 131732723HCID 131732723, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-methoxy acetophenone (104.16 mg, 0.694 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, 0.694 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 (6z) (266 mg, 91% 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-862b9fc37df94ff8880f6ea0e62568f7
Source dataset
uspto-grants-2015_04
Patent number
US09006451B1

Reaction notes

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