Dimethylformamide → 2,3-Dihydro-2-(phenylmethyl)-1H-isoindole-4-carboxamide

HRID 1494850Notes

Reaction equation

HRID 1494850 reaction equation
[CH2:1]([N:8]1[CH2:16][C:15]2[C:14]([C:17]([OH:19])=O)=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C[N:25](C=O)C>>[CH2:1]([N:8]1[CH2:16][C:15]2[C:14]([C:17]([NH2:25])=[O:19])=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 221368252-Benzyl-2,3-dihydro-1H-isoindole-4-carboxylic acid

Product 1

HCID 198284812,3-Dihydro-2-(phenylmethyl)-1H-isoindole-4-carboxamide

Procedure

A mixture of 35.0 g of 2-benzylisoindoline-4-carboxylic acid, 150 ml of thionyl chloride, and 1 ml of DMF was heated under reflux for 10 hours. After cooling, the reaction mixture was concentrated to the extent that the acid chloride crystals does not deposit. To the concentrate was added dropwise 28% aqueous ammonia under ice cooling and stirring After stirring for 3 hours crystals produced was collected by filtration and washed with water. The crystals were dissolved in chloroform, washed with 5% sodium hydroxide and water, and concentrated. The residue was recrystallized from ether to obtain 24.1 g of 2-benzylisoindoline-4-carboxamide.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated to the extent that the acid chloride crystals
  5. additionTo the concentrate was added dropwise 28% aqueous ammonia under ice cooling
  6. stirringAfter stirring for 3 hours crystals
  7. customproduced
  8. filtrationwas collected by filtration
  9. washwashed with water
  10. dissolutionThe crystals were dissolved in chloroform
  11. washwashed with 5% sodium hydroxide and water
  12. concentrationconcentrated
  13. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-86ddc622b85b498e8395d8a3cacc2c8b
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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