Hydrochloric Acid → HCID 123311578, compound

HRID 1470538Notes

Reaction equation

HRID 1470538 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([C:15](=[O:17])[CH3:16])=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29])[CH:23]=O.COC1C=CC(NC2C(C=CC(C3C=C(OC)C(OC)=C(OC)C=3)=O)=CC=CN=2)=CC=1.Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:14]([C:15](=[O:17])[CH:16]=[CH:23][C:22]3[CH:25]=[C:26]([O:30][CH3:31])[C:27]([O:28][CH3:29])=[C:20]([O:19][CH3:18])[CH:21]=3)=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 68583,4,5-TrimethoxybenzaldehydeHCID 117992380HCID 117992380, compoundHCID 131732719HCID 131732719, compound

Product 1

HCID 123311578HCID 123311578, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(2-(4-chlorophenylamino)pyridin-3-yl)ethanone (100 mg, 0.406 mmol) in methanol (5 mL) was added 2N Ba(OH)2 solution (2 ml) and stirred for 5 minutes. Then added 3,4,5-trimethoxybenzaldehyde (79.65 mg, 0.406 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 (7h) (147 mg, 85% 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-4e83fc957c7245aa895eb42069c99def
Source dataset
uspto-grants-2015_04
Patent number
US09006451B1

Reaction notes

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