Formic Acid → N-Formylindoline

HRID 50118Notes

Reaction equation

HRID 50118 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]>ClCCl>[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-Formylindoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of indoline (10 g, 840 mmol) in dichloromethane (400 mL) was treated with 88% formic acid (48.8 g, 924 mmol), heated to reflux, and stirred for 2.5 hours. The mixture was concentrated to 2/3 of the original volume, diluted with 1,2-dichloroethane (200 mL), and again concentrated to 2/3 of the original volume to provide a solution of N-formylindoline in 1,2-dichloroethane, which was used without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. concentrationThe mixture was concentrated to 2/3 of the original volume
  4. additiondiluted with 1,2-dichloroethane (200 mL)
  5. concentrationagain concentrated to 2/3 of the original volume

Sources & evidence

ORD record
ord-bdb3f77f0e9642d39d90708bea6e3e07
Source dataset
uspto-grants-2004_03
Patent number
US06710185B2

Reaction notes

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