Sodium Hydroxide → Indoline
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customInto a 100 ml reaction flask
- customequipped with a condenser
- customreacted at 110° C. for 8 hours
- customThe reaction mixture thereby obtained
- customwas subjected to liquid separation
- customto separate the aqueous layer from the organic layer
- washThe organic layer was washed with an acid
- distillationdistilled
Sources & evidence
- ORD record
- ord-017309f48c9c4798849388dba673aff3
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04673749
Reaction notes
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