Aniline → 4-(1,4-Dihydroindeno[1,2-c]pyrazol-3-yl)benzanilide

HRID 990992Notes

Reaction equation

HRID 990992 reaction equation
[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.C(Cl)(=O)C(Cl)=O.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C>CN(C)C=O.ClCCl>[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:18])=[CH:15][CH:14]=2)=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

7

Reactant 4

HCID 6115AnilineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 184158474-(1,4-Dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid

Product 1

HCID 184160004-(1,4-Dihydroindeno[1,2-c]pyrazol-3-yl)benzanilide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
17.5 °C

Procedure

A mixture of 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid (0.37 g), dichloromethane (20 ml) and oxalyl chloride (0.26 ml) was stirred at 15-20° C. and then dimethylformamide (3 drops) was added. The mixture was stirred at 15-20° C. for 30 minutes and then warmed at 40° C. for 1 hour. The solvent was removed under reduced pressure to give a solid which was dissolved in dichloromethane (20 ml) and then aniline (0.13 ml) and triethylamine (0.38 ml) were added. The mixture was stirred at ambient temperature under nitrogen for 2 hours and then washed with water, dried, filtered and evaporated to give a solid which was purified by flash column chromatography on silica to give 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzanilide, m.p. 186-190° C.

Workup

  1. stirringThe mixture was stirred at 15-20° C. for 30 minutes
  2. temperaturewarmed at 40° C. for 1 hour
  3. customThe solvent was removed under reduced pressure
  4. customto give a solid which
  5. stirringThe mixture was stirred at ambient temperature under nitrogen for 2 hours
  6. washwashed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customto give a solid which
  11. customwas purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-439c3b0e848345629d60be221d2b2ffc
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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