Hydrochloric Acid → HCID 178443739, compound

HRID 227331Notes

Reaction equation

HRID 227331 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:15])[CH3:14])=[CH:10][CH:11]=2)[CH2:6][C:5]1=[O:16])(=[O:3])[CH3:2].CN(C1C=CC=CN=1)C.[C:26](Cl)(=[O:34])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].Cl>CN(C)C=O.C(Cl)Cl.C(N(CC)CC)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:15])[CH3:14])=[CH:10][CH:11]=2)[C:6](=[C:26]([OH:34])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[C:5]1=[O:16])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8124Octanoyl chlorideHCID 218852-DimethylaminopyridineHCID 210845601,5-Diacetyl-2-indolinone

Product 1

HCID 178443739HCID 178443739, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4.3 g (20 mmol) 1,5-diacetyl-2-indolinone (Ex. II) are dissolved in 20 ml of dimethylformamide and 490 mg dimethylaminopyridine (DMAP) and 6 ml triethylamine added and the mixture is cooled in the ice bath. 3.8 ml (22 mmol) octanoic acid chloride in 20 ml of dimethylformamide are added to this solution and the mixture is stirred for a further 10 min. Then the reaction mixture is added to 150 ml of methylene chloride and 150 ml 1 N hydrochloric acid. The organic phase is separated off, dried over sodium sulphate and concentrated by rotary evaporation. The residue is chromatographed through a silica gel column with methylene chloride/methanol 95:5.

Workup

  1. customThe organic phase is separated off
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated by rotary evaporation
  4. customThe residue is chromatographed through a silica gel column with methylene chloride/methanol 95:5

Sources & evidence

ORD record
ord-f3f28071f9a843b683abb9f55074393e
Source dataset
uspto-grants-2009_07
Patent number
US07560480B2

Reaction notes

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