Hydrochloric Acid → HCID 178443739, compound

HRID 347995Notes

Reaction equation

HRID 347995 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 are 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 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-ccce9db409004e44822bf519cd9fb1a4
Source dataset
uspto-grants-2007_02
Patent number
US07176231B2

Reaction notes

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