Aniline → HCID 14843023, compound

HRID 1614196Notes

Reaction equation

HRID 1614196 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([OH:23])=O)=O)=[CH:2]1.[NH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][C:12]2[N:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:21](=[O:23])[C:16]3[C:15](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:14]=2)=[CH:2]1

Participants

5

Reactant 3

HCID 6115AnilineHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 3749947HCID 3749947, compound

Product 1

HCID 14843023HCID 14843023, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-indolyl)-N-(2-carboxyphenyl)propionamide (6.20 g, 20 mmol) in 50 ml of THF at room temperature was added 1,1-carbonyldiimidazole (3.26 g, 20 mmol). The reaction mixture was stirred under a dry atmosphere for 30 minutes after which aniline (2 ml, 22 mmol) and PPTS (4.03 g, 16 mmol) were added. The resulting reaction mixture was stirred under reflux for two days. The reaction mixture was allowed to cool and evaporated to dryness in vacuo. The product residue was taken up in ethyl acetate and washed (1N HCl, water, saturated NaHCO3, and brine), dried over anhydrous sodium sulfate, and concentrated in vacuo to a brown oil which crystallized from ethyl acetate/hexanes. The product was recrystallized from methanol/ethyl acetate to provide 2.28 g of 2-[2-(3-indolyl)ethyl]-3-phenyl-4-(3H)quinazolinone as white fluffy needles; m.p. 193°-194° C.; FABMS and EIMS 366 (M+); IR (KBr) 1672 CM-1.

Workup

  1. additionwere added
  2. customThe resulting reaction mixture
  3. temperatureunder reflux for two days
  4. temperatureto cool
  5. customevaporated to dryness in vacuo
  6. washwashed (1N HCl, water, saturated NaHCO3, and brine)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo to a brown oil which
  9. customcrystallized from ethyl acetate/hexanes
  10. customThe product was recrystallized from methanol/ethyl acetate

Sources & evidence

ORD record
ord-9842a3d826ba4b9097906b115d72ca08
Source dataset
uspto-grants-1993_03
Patent number
US05196427

Reaction notes

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