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Chemical Structure| 29217-11-6 Chemical Structure| 29217-11-6

Structure of 29217-11-6

Chemical Structure| 29217-11-6

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Product Details of [ 29217-11-6 ]

CAS No. :29217-11-6
Formula : C11H12N2O
M.W : 188.23
SMILES Code : C/C=N/OC1=CN(C)C2=C1C=CC=C2

Safety of [ 29217-11-6 ]

Application In Synthesis of [ 29217-11-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 29217-11-6 ]

[ 29217-11-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 19012-02-3 ]
  • [ 29217-11-6 ]
YieldReaction ConditionsOperation in experiment
With hydroxylamine hydrochloride; sodium acetate; In ethanol; water; for 2.5h;Heating / reflux; To a mixture of 3-acetylindole 1 (0.157 mol, 25.0 g) in DMF (200 ml) was added potassium carbonate (1.05 equiv. , 0.165 mol, 22.8 g) and methyl iodide (1. 1 equiv. , 0.173 mol, 24.5 g). The mixture was stirred at room temperature overnight. To the mixture was added potassium carbonate (2.1 equiv. , 0.330 mol, 45.6 g) and methyl iodide (2.2 equiv. , 0.346 mol, 49.0 g). The mixture was stirred at room temperature for 3 hours. The mixture was concentrated under reduced pressure to 1/5 THE original volume. The residue was dissolved in dichloromethane and washed with water. The organic phase was dried with MGS04, concentrated in vacuo, affording intermediate m (purity (LC) = 90%). The crude product was used without further purification in the next step. To a mixture of intermediate m (0.312 mol, 54. 0G) in ethanol (150 ml and water (100 ml) was added acetic acid, sodium salt (2.4 equiv. , 0.748 mol, 61.0 g) and hydroxyl- amine hydrochloride (3 equiv. , 0.935 mol, 65.0 g). The mixture was stirred and heated at reflux for 2.5 hours. The mixture was cooled to room temperature. The reaction mixture was poured into water (750 ml). The precipitate was isolated by filtration and washed with water. The crude precipitate was dissolved in THF (200 ml) and toluene (50 ml) and the mixture was evaporated to dryness (2x), affording intermediate n (purity (LC) = 80 %). The crude product was used as such in the next reaction. Intermediate n (0.312 mol, 58.7g) was dissolved in acetic acid (300 ml). The mixture was stirred and heated at reflux for 2 hours. The mixture was concentrated in vacuo. Toluene (100 ml) added and evaporated to dryness (2x). Crystallization from ethanol (400 ml) gave crude intermediate p (31. 0 g, purity (LC) = 90%). RECRYSTALLIZATION in ethanol (300 ml) afforded p [C. PAPAMICAEL, G. QUeGUINER, J. Bourguignon, G. Dupas Tetrahedron 2001, 57, 5385-5391] as brown crystals (29.4 g, yield = 50%, purity (LC) > 98%). To cooled (0C) dry DMF (40 ML) was added dropwise phosphorus oxychloride (2.5 equiv. , 0.199 mol, 30.6 g) and the reaction mixture was stirred for 0. 5h at 0C. Then, a solution of p (0.080 mol, 15.0 g) in DMF (160 ML) was added. The cooling was removed and the reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was poured into ice-water (21) and stirred for 0.5 hours. A brown precipitate was isolated by filtration and washed with water. The precipitate was dried for 24 hours in open air, affording intermediate q as a brown powder (6.10 g, yield = 35%, purity (LC) = 95%). A mixture of intermediate q (0.005 mol, 1.13 g), Pd/C-catalyst (10%, 0.50 g) and triethylamine (6.8 equiv. , 0.036 mol, 3.60 g) in TH : F (200 ml) was hydrogenated at atmospheric pressure for 2 hours. The catalyst was removed by filtration. The filtrate was evaporated to give r as a brown powder (0.88g, yield = 92%, purity (LC) > 95%). To a mixture of intermediate r (0.005 mol, 0.880 g) and ethanol (5 ml) was added 3-chloroperoxybenzoic acid (70-75 %, 1.2 equiv. , 0.006 mol, 1.43g). The reaction mixture was heated at reflux for 2 hours. Pyridine (0.5 equiv. , 0.002 mol, 0.190 g) was added and the mixture was heated at reflux for 0. 5H. The reaction mixture was cooled to room temperature and evaporated in vacuo to dryness. The residue was mixed with acetic anhydride (10 ml) and heated at reflux for 4 h and evaporated to dry. The residue was dissolved in 2N potassium hydroxide (50 ml) and stirred for LH. The pH of the reaction mixture was adjusted to 1 by the addition of concentrated hydrochloric acid. A brown precipitate was isolated by filtration. The precipitate was washed with a saturated sodium bicarbonate solution (2x 10 ml), water, isopropanol and diisopropyl ether, affording intermediate s as a brown powder (0.680 g, yield = 71 %, purity (LC) >95%). A mixture OF S (0.001 mol, 0.2 g), copper (II) acetate (2 equiv. , 0.002 mol, 0.366g), 4-acetylphenylboronic acid (2 equiv. , 0.002 mol, 0.328 g) and powdered molecular sieves (4A) in DMF/PYRIDINE (9/1) (3ML) was heated in a stoppered flask at 80C overnight. The molecular sieves were removed by filtration and washed with acetonitrile. The combined filtrates was evaporated under reduced pressure and the crude mixture was purified with by preparative HPLC affording compound 122 (0.066g, yield= 21%, purity (LC) >95%).
With hydroxylamine hydrochloride; sodium acetate; In ethanol; water; for 2.5h;Heating / reflux; To a mixture of intermediate b (0.312 mol, 54.0g) in ethanol (150 ml) and water (100 ml) was added acetic acid, sodium salt (2.4 equiv. , 0.748 mol, 61.0 g) and hydroxyl- amine hydrochloride (3 equiv. , 0.935 mol, 65.0 g). The mixture was stirred and heated at reflux for 2.5 hours and subsequently cooled to room temperature. The reaction mixture was poured into water (750 ml). The precipitate was isolated by filtration and washed with water. The crude precipitate was dissolved in THF (200 ml) and toluene (50 ml) and the mixture was evaporated, affording intermediate c (purity (LC)= 80 %). The crude product was used as such in the next reaction.
With hydroxylamine; sodium acetate; In ethanol; water; for 2.5h;Heating / reflux; To a mixture of intermediate m (0.312 mol, 54.0g) in ethanol (150 ml and water (100 ml) was added acetic acid, sodium salt (2.4 equiv. , 0.748 mol, 61.0 g) and hydroxyl- amine hydrochloride (3 equiv. , 0.935 mol, 65.0 g). The mixture was stirred and heated at reflux for 2.5 hours. The mixture was cooled to room temperature. The reaction mixture was poured into water (750 ml). The precipitate was isolated by filtration and washed with water. The crude precipitate was dissolved in THF (200 ml) and toluene (50 ml) and the mixture was evaporated to dryness (2x), affording intermediate n (purity (LC) = 80 %). The crude product was used as such in the next reaction.
  • 2
  • [ 19012-02-3 ]
  • [ 29217-11-6 ]
  • 3-acetyl-1-methylindole, (Z)-oxime [ No CAS ]
  • 3
  • [ 19012-02-3 ]
  • [ 29217-11-6 ]
  • [ 3265-24-5 ]
  • [ 85729-26-6 ]
 

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