Formic Acid → N-Formylindoline

HRID 583921Notes

Reaction equation

HRID 583921 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH:10](O)=[O:11]>C1(C)C=CC=CC=1>[CH:10]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)=[O:11]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 10328Indoline

Product 1

HCID 576501N-FormylindolineYield 89.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of indoline (5.0 g) and 98% formic acid (3.0 g) in toluene (17 mL) was heated at reflux for 6 hours with a Dean-Stark trap, cooled, washed with water and concentrated. The resulting dark brown solid was dissolved in methanol, concentrated to a fraction of its original volume, treated with 1:1 diethyl ether/hexane, and concentrated dryness to provide 5.5 g of the desired product.

Workup

  1. temperatureat reflux for 6 hours with a Dean-Stark trap
  2. temperaturecooled
  3. washwashed with water
  4. concentrationconcentrated
  5. dissolutionThe resulting dark brown solid was dissolved in methanol
  6. concentrationconcentrated to a fraction of its original volume
  7. additiontreated with 1:1 diethyl ether/hexane
  8. concentrationconcentrated dryness

Sources & evidence

ORD record
ord-a1a3367a5e784c47971c1e3cf1910163
Source dataset
uspto-grants-2005_08
Patent number
US06924304B2

Reaction notes

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