Water → HCID 4448611, compound

HRID 1278928Notes

Reaction equation

HRID 1278928 reaction equation
C(N(CC)CC)C.[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=1)[CH:21]=[CH:22][C:23](Cl)=[O:24].O>C(Cl)Cl>[Cl:17][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][C:23]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9]2)=[O:24])[CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10328IndolineHCID 53411290HCID 53411290, compound

Product 1

HCID 4448611HCID 4448611, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

Triethylamine (9.2 ml) was added at room temperature to a solution of indoline (20 g) in DCM (200 ml) and the mixture was cooled till 5° C. A solution of m-chlorocinnamoyl chloride (40 g) in DCM (100 ml) was added dropwise and the mixture was stirred at room temperature for 48 hours. Water was added, the organic layer was decanted, washed with water, dried, filtered off and evaporated. The residue was purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate 90/10), yielding 41 g (73%) of 1-[3-(3-chlorophenyl)-1-oxo-2-propenyl]-2,3-dihydro-1H-indole (interm. 37).

Workup

  1. customthe organic layer was decanted
  2. washwashed with water
  3. customdried
  4. filtrationfiltered off
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate 90/10)

Sources & evidence

ORD record
ord-d46c3ccfc544455e94a79d5fd0e05ddc
Source dataset
uspto-grants-2002_09
Patent number
US06444812B1

Reaction notes

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