Hydrochloric Acid → HCID 123437096, compound

HRID 1470534Notes

Reaction equation

HRID 1470534 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].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]2[N:31]=[CH:30][CH:29]=[CH:28][C:25]=2[CH:26]=O)=[CH:19][CH:18]=1.COC1C=CC(NC2C(C=CC(C3C=C(OC)C(OC)=C(OC)C=3)=O)=CC=CN=2)=CC=1.Cl>CO>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]2[C:25]([CH:26]=[CH:1][C:2]([C:4]3[CH:5]=[C:6]([O:14][CH3:15])[C:7]([O:12][CH3:13])=[C:8]([O:10][CH3:11])[CH:9]=3)=[O:3])=[CH:28][CH:29]=[CH:30][N:31]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 143453',4',5'-TrimethoxyacetophenoneHCID 18956137HCID 18956137, compoundHCID 131732719HCID 131732719, compound

Product 1

HCID 123437096HCID 123437096, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,4,5-trimethoxyacetophenone (135 mg, 0.06465 mmol) in methanol (5 mL) was added 2N Ba(OH)2 solution (2 mL) and stirred for 5 minutes. Then added 2-(4-chlorophenylamino)nicotinaldehyde (150 mg, 0.0.6465 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 (6ax) (232 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
  5. customto obtain pure (6ax) (232 mg, 85% yield)

Sources & evidence

ORD record
ord-36fca0b55b124d899224fb726d5dd8ac
Source dataset
uspto-grants-2015_04
Patent number
US09006451B1

Reaction notes

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