Sodium Hydroxide → 1-[2-(Phenylmethyl)-1H-indol-3-yl]ethanone

HRID 2270967Notes

Reaction equation

HRID 2270967 reaction equation
[CH3:1][C:2](N(C)C)=[O:3].P(Cl)(Cl)(Cl)=O.[CH2:12]([C:19]1[NH:20][C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>>[C:2]([C:27]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][C:19]=1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:3])[CH3:1]

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 31374DimethylacetamideHCID 111274792-(Phenylmethyl)-1H-indole

Product 1

HCID 129686341-[2-(Phenylmethyl)-1H-indol-3-yl]ethanoneYield 53%

Procedure

To a solution of 29.5 g (39 mmol) of dimethylacetamide was added dropwise under ice-cooling 7.00 g (76.9 mmol) of phosphorus oxychloride. After stirring for 30 min at room temperature, to the mixture was added 8.00 g (38.6 mmol) of 2-benzylindole (prepared in accordance with the literature (Khim.Geterotsikl.Soedin.1994,p133)). After stirring for 2 hours at 100° C., the mixture was poured to ice-water, neutralized with 2N NaOH, extracted with ethyl acetate. The extract was washed with water, dried, and concentrated. The obtained crystal was washed with n-hexane to give 5.1 g of the titled compound. Yield: 52%.

Workup

  1. customprepared in accordance with the literature (Khim.Geterotsikl.Soedin.1994,p133))
  2. stirringAfter stirring for 2 hours at 100° C.
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated
  7. washThe obtained crystal was washed with n-hexane

Sources & evidence

ORD record
ord-020b2000eff346e6b6f3553d6363f9ec
Source dataset
uspto-grants-2001_12
Patent number
US06333323B1

Reaction notes

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