Sodium Hydroxide → Indoline

HRID 652827Notes

Reaction equation

HRID 652827 reaction equation
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][NH2:6].[OH-].[Na+]>[Cu].N1C2C(=CC=CC=2)C=CC=1>[NH:6]1[C:7]2[C:3](=[CH:2][CH:10]=[CH:9][CH:8]=2)[CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 831172-(2-Chlorophenyl)ethylamine

Product 1

HCID 10328IndolineYield 96%

Reagents, catalysts & solvents 1

HCID 67118996Copper quinolineCatalyst

Procedure

Into a 100 ml reaction flask equipped with a condenser, a thermometer and a stirrer, 15.56 g (0.1 mol) of 2-chlorophenethylamine, 22.0 g (0.11 mol) of a 20% sodium hydroxide aqueous solution and 0.176 g (0.5 mol %) of quinoline copper were charged, and reacted at 110° C. for 8 hours. The reaction mixture thereby obtained was subjected to liquid separation to separate the aqueous layer from the organic layer. The organic layer was washed with an acid and distilled to obtain 11.4 g of indoline (boiling point: 94°-95° C./11 mmHg). The purity was 99.5%, and the yield was 96%.

Workup

  1. customInto a 100 ml reaction flask
  2. customequipped with a condenser
  3. customreacted at 110° C. for 8 hours
  4. customThe reaction mixture thereby obtained
  5. customwas subjected to liquid separation
  6. customto separate the aqueous layer from the organic layer
  7. washThe organic layer was washed with an acid
  8. distillationdistilled

Sources & evidence

ORD record
ord-017309f48c9c4798849388dba673aff3
Source dataset
uspto-grants-1987_06
Patent number
US04673749

Reaction notes

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