N-[2-(2,3-Dihydro-1H-indol-1-yl)-5-methylphenyl]formamide → HCID 14459746, compound

HRID 1904927Notes

Reaction equation

HRID 1904927 reaction equation
[CH:1]([NH:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1)=O>P(Cl)(Cl)(Cl)=O>[CH3:10][C:8]1[CH:7]=[CH:6][C:5]2[N:11]3[CH2:12][CH2:13][C:14]4[C:19]3=[C:18]([CH:17]=[CH:16][CH:15]=4)[CH:1]=[N:3][C:4]=2[CH:9]=1

Participants

3

Reactant 1

HCID 14459745N-[2-(2,3-Dihydro-1H-indol-1-yl)-5-methylphenyl]formamide

Product 1

HCID 14459746HCID 14459746, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

1-(2-Formamido-4-methylphenyl)indoline (34 gm) in phosphorous oxychloride (220 ml) was heated at 100° C. (steam bath) for 2.5 hours, during which the product precipitated. The mixture was cooled to room temperature and ether (400 ml) was added and the excess phosphorous oxychloride was removed by filtration. The solids were washed with ether (3×400 ml) and thereafter dissolved in a mixed solvent of 10% triethylamine/dichloromethane (1.2 L). The organic solution was washed with 10% sodium hydroxide solution (350 ml), water (400 ml) and brine (600 ml), and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to leave an oil (28 gm). The oil was purified by flash chromatography over silica gel (320 gm, eluted with dichloromethane, 6 L). The resultant oil turned into crystals on shaking with ether (150 ml). The crystals were collected and dried to afford 25.9 gm, m.p. 77°-78° C.

Workup

  1. customduring which the product precipitated
  2. additionether (400 ml) was added
  3. customthe excess phosphorous oxychloride was removed by filtration
  4. washThe solids were washed with ether (3×400 ml)
  5. dissolutiondissolved in a mixed solvent of 10% triethylamine/dichloromethane (1.2 L)
  6. washThe organic solution was washed with 10% sodium hydroxide solution (350 ml), water (400 ml) and brine (600 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c2cb32f255f0463ca85917510f0b3b0b
Source dataset
uspto-grants-1989_06
Patent number
US04840947

Reaction notes

Loading…