Potassium Hydroxide → HCID 13958097, compound
Reaction equation
O.NN.[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=O)[CH2:12][CH2:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[CH:17][NH:18]2.[OH-].[K+]>C(O)COCCO>[NH:18]1[C:19]2[C:15](=[C:14]([CH2:13][CH2:12][CH2:11][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[OH:4])[CH:22]=[CH:21][CH:20]=2)[CH:16]=[CH:17]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
22.6 ml of hydrazine hydrate and then 11.6 g of 1-(2-hydroxyphenyl)-3-(1H-indol-4-yl)-1-propanone were slowly added with stirring to 50 ml of diethyleneglycol and then 20 ml of 78% potassium hydroxide were added thereto. The mixture was heated at 140° C. under an inert atmosphere for 30 minutes and the water and excess hydrazine hydrate were distilled at 210° C. with stirring over two hours and the mixture was cooled and diluted with water. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried, filtered and evaporated to dryness. The residue was chromatographed over silica and eluted with methylene chloride to obtain 8.613 g of 2-[3-(1H-indol-4-yl)-propyl]-phenol melting at ≅89° C.
Workup
- distillationthe water and excess hydrazine hydrate were distilled at 210° C.
- temperaturethe mixture was cooled
- additiondiluted with water
- extractionThe mixture was extracted with ethyl acetate
- washthe organic phase was washed with water
- customdried
- filtrationfiltered
- customevaporated to dryness
- customThe residue was chromatographed over silica
- washeluted with methylene chloride
Sources & evidence
- ORD record
- ord-f168c041e94d46beae0d5f44032750f1
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04808609
Reaction notes
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