HCID 14459753, compound → HCID 14459754, compound

HRID 1904933Notes

Reaction equation

HRID 1904933 reaction equation
[N:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1>P(Cl)(Cl)(Cl)=O>[N:22]1[CH:23]=[CH:24][C:19]([C:17]2[C:8]3[CH:7]=[CH:6][CH:5]=[C:4]4[CH2:3][CH2:2][N:1]([C:9]=34)[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:16]=2)=[CH:20][CH:21]=1

Participants

3

Reactant 1

HCID 14459753HCID 14459753, compound

Product 1

HCID 14459754HCID 14459754, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

N-[2-(2,3-dihydro-1H-indol-1-yl)phenyl]-4-pyridinecarboxamide (10 gm) in phosphorous oxychloride (300 ml) was refluxed under nitrogen for 4.5 hours. Themixture was cooled to room temperature. The excess of phosphorous oxychloride was removed under reduced pressure (55° C.). The residue was partitioned between dichloromethane and 10% sodium hydroxide solution (600 ml:600 ml). The organic phase was separated and washed with water (250 ml) and brine (2×500 ml). The solution was dried over anhydrous magnesium sulfate and concentrated to about 10 gm of gum. Purification was effected by flash chromatography (silica, 150 gm, eluted with 1.5% methanol/98.5% dichloromethane, 4 L) to yield 6.7 gm of solid. Recrystallization from hot ethanol (70 ml) yielded 5.24 gm of crystals, m.p. 152°-153° C.

Workup

  1. customThe excess of phosphorous oxychloride was removed under reduced pressure (55° C.)
  2. customThe residue was partitioned between dichloromethane and 10% sodium hydroxide solution (600 ml:600 ml)
  3. customThe organic phase was separated
  4. washwashed with water (250 ml) and brine (2×500 ml)
  5. dry with materialThe solution was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated to about 10 gm of gum
  7. customPurification
  8. washwas effected by flash chromatography (silica, 150 gm, eluted with 1.5% methanol/98.5% dichloromethane, 4 L)

Sources & evidence

ORD record
ord-ddb1123bbd6949c4ae515f41cc56fe57
Source dataset
uspto-grants-1989_06
Patent number
US04840947

Reaction notes

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