Hydrochloric Acid → HCID 123736608, compound

HRID 1470533Notes

Reaction equation

HRID 1470533 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].[F: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>[F: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 13958146HCID 13958146, compoundHCID 131732719HCID 131732719, compound

Product 1

HCID 123736608HCID 123736608, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,4,5-trimethoxyacetophenone (194 mg, 0.925 mmol) in methanol (5 mL) was added 2N Ba(OH)2 solution (2 ml) and stirred for 5 minutes followed by the addition of 2-(4-fluorophenylamino)nicotinaldehyde (200 mg, 0.925 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 (6aj) (340 mg, 90% 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 (6aj) (340 mg, 90% yield)

Sources & evidence

ORD record
ord-dfe1391ea9514f619d7753f3974263c8
Source dataset
uspto-grants-2015_04
Patent number
US09006451B1

Reaction notes

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