Formic Acid → N-Formylindoline

HRID 2099551Notes

Reaction equation

HRID 2099551 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].O>C1(C)C=CC=CC=1>[N:1]1([CH:10]=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 10328Indoline

Product 1

HCID 576501N-Formylindoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of indoline (47.4 g, 398 mmol) and formic acid (30 g, 652 mmol, 1.64 eq.) in toluene (175 mL) was heated at reflux with azeotropic removal of water. After 3 h, the reaction mixture was cooled to RT. The solution was washed with water and brine, dried over Na2SO4 and concentrated. The residue was triturated with TBME and heptanes. The precipitate was filtered off, washed with heptanes and pentane and dried in vacuo at 45° C. for 4 h. Yield: 50.46 g, (86%).

Workup

  1. washThe solution was washed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was triturated with TBME and heptanes
  5. filtrationThe precipitate was filtered off
  6. washwashed with heptanes and pentane
  7. customdried in vacuo at 45° C. for 4 h

Sources & evidence

ORD record
ord-f7e0d8e165fb44cbb8ba02a37941c856
Source dataset
uspto-grants-2009_08
Patent number
US07569604B2

Reaction notes

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