Bromobenzene → 2,3-dihydro-1H-indol-7-yl(phenyl)methanone

HRID 267236Notes

Reaction equation

HRID 267236 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([OH:12])=O)[CH2:3][CH2:2]1.[C:13]1([Li])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.BrC1C=CC=CC=1.[Li]>CCOCC>[C:10]([C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[NH:1][CH2:2][CH2:3]2)(=[O:12])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 7961BromobenzeneHCID 3028194LithiumHCID 127011472,3-Dihydro-1H-indole-7-carboxylic acidHCID 178506676HCID 178506676, compound2×

Product 1

HCID 27418922,3-dihydro-1H-indol-7-yl(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A stirred mixture of 0.165 mole (25 g.) of indoline-7-carboxylic acid and 800 ml. of dry ether was treated dropwise with 0.435 mole of phenyllithium which was prepared from 157 g. (0.435 mole) of bromobenzene, 6.94 g. (0.87 mole) of lithium wire and 500 ml. of dry ether. After addition of the phenyllithium, the reaction mixture was refluxed for three hours and then poured onto ice. After warming to room temperature, the mixture was filtered and the ether layer was separated from the aqueous layer. After washing the ether extract with 1N hydrochloric acid, the product was extracted into 12 N hydrochloric acid. Neutralization of the acidic extract caused precipitation of crude product. The product melted at 119°-122°C.

Workup

  1. customwas prepared from 157 g
  2. temperaturethe reaction mixture was refluxed for three hours
  3. additionpoured onto ice
  4. filtrationthe mixture was filtered
  5. customthe ether layer was separated from the aqueous layer
  6. washAfter washing the ether
  7. extractionextract with 1N hydrochloric acid
  8. extractionthe product was extracted into 12 N hydrochloric acid
  9. extractionNeutralization of the acidic extract
  10. customprecipitation of crude product

Sources & evidence

ORD record
ord-27358f5ea68e421e91664106cd703946
Source dataset
uspto-grants-1976_03
Patent number
US03941806

Reaction notes

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