Formic Acid → N-Formylindoline

HRID 1809330Notes

Reaction equation

HRID 1809330 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>[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

5

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 10328Indoline

Product 1

HCID 576501N-FormylindolineYield 91.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of indoline (145 g, 1.2 mol) and formic acid (90%, 92 g, 1.8 mol) was brought to reflux in toluene with removal of water via a Dean-Stark apparatus. After 6 hours the reaction mixture was cooled to room temperature, washed with water and concentrated in vacuo. N-formylindoline (158 g, 1.1 mol, 88% yield) was isolated as an off-white solid and used in the next step without further purification. Mixture of rotamers: 1H-NMR (CDCl3) δ 8.92 (s, 0.85H), 8.51 (s, 0.15H), 8.06 (d, J=8.3 Hz, 0.15H), 7.26-7.16 (m, 3.85H), 7.16-7.02 (m, 1H), 4.13-4.02 (m, 2H), 3.21-3.12 (dt, 2H).

Workup

  1. washwashed with water
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b95776d3891e453db9108ee9765f3420
Source dataset
uspto-grants-2013_01
Patent number
US08362032B2

Reaction notes

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