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Chemical Structure| 77802-37-0 Chemical Structure| 77802-37-0

Structure of 77802-37-0

Chemical Structure| 77802-37-0

N-(2,3-Dihydro-1H-inden-4-yl)acetamide

CAS No.: 77802-37-0

4.5 *For Research Use Only !

Cat. No.: A767450 Purity: 95%

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Product Details of [ 77802-37-0 ]

CAS No. :77802-37-0
Formula : C11H13NO
M.W : 175.23
SMILES Code : CC(NC1=CC=CC2=C1CCC2)=O

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Application In Synthesis of [ 77802-37-0 ]

* 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 [ 77802-37-0 ]

[ 77802-37-0 ] Synthesis Path-Downstream   1~3

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  • [ 32202-61-2 ]
  • [ 64-19-7 ]
  • [ 77802-37-0 ]
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YieldReaction ConditionsOperation in experiment
100% In ethanol; at 0 - 20℃; for 3h; To a stirring solution of acetic anhydride (14 mL, 278 mmol) in EtOH (150m1) was addedthe solution of <strong>[32202-61-2]2,3-dihydro-1H-inden-4-amine</strong> SM (10 g, 75 mmol) in EtOH (50 mL) at 0 C andstirred at room temperature for 3 hours. After consumption of the starting material (by TLC), the solvent from reaction mixture was removed under reduced pressure to afford compound 1 (13.1 g, 100%) as an off-white solid used for next step directly. LC-MS: m/z = 176.2 [M+H]
98.9% In ethanol; at 0 - 20℃; for 1h; Example 19: Synthesis of Compound XIII-30; Step 1 : Synthesis of N-(2-3-dihydro-lH-inden-4-yl)acetamide (2); To a solution of 4-amino indane (1, 5 g, 37.5 mmol) in ethanol ( 1 1 1 mL) was taken, acetic anhydride (7.3 mL, 74.8 mmol) in ethanol (20 mL) was added drop wise at 0 C and stirred at RT for 1 h. Reaction was monitored by TLC. After completion of the reaction, ethanol was evaporated under reduced pressure, triturated with diethyl ether to afford N-(2,3-dihydro-l H-inden-4-yl)acetamide as off-white solid (2, 6.5 g, 98.9%) NMR (400 MHz, CDCI3): delta 7.80-7.70 (d, 1 H), 7.20-7. 10 (t, 1H), 7.10-7.00 (d, 1 H), 3.00-2.90 (t, 2H), 2.90-2.70 (t, 2H), 2.21 (s, 3H), 2.20-2.10 (t, 2H).
97.1% In ethanol; at 0 - 20℃; for 12h; A solution of <strong>[32202-61-2]4-aminoindan</strong> (13.5 g, 101 mmol) was added to a 500 mL round bottom flask, 50 mL of ethanol was added, dissolved with stirring and cooled to 0 C. Then, 200 mL of an ethanol solution in which acetic anhydride (19 mL, 201 mmol) was dissolved was added, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was distilled off under reduced pressure to obtain 17.0 g of a white solid. Yield 97.1%
97.1% In ethanol; at 0 - 20℃; for 12h; A mixture of <strong>[32202-61-2]4-aminoindan</strong> (13.5g, 101mmol) was added to a 500mL round bottom flask was added 50mL of ethanol was stirred and cooled to 0 deg.] C to dissolve, then added a solution of acetic anhydride (19mL, 201mmol) in ethanol 200 mL, room temperature stirred for 12 hours; the reaction was completed, the solvent was distilled off under reduced pressure to give a white solid 17.0 g, yield 97.1%.
96.7% With triethylamine; In dichloromethane; at 0 - 16℃; for 1.5h; To a solution of <strong>[32202-61-2]2,3-dihydro-1H-inden-4-amine</strong> (19.8 g, 148.66 mmol, i eq) and TEA(19.56 g, 193.26 mmol, 26.90 mL, 1.3 eq) in DCM (300 mL) was added dropwise Ac20(17.45 g, 170.96 mmol, 16.01 mL, 1.15 eq) over 0.1 hour at 0 C. Then the reactionmixture was warmed to 16 C and stirred for 1.4 hours. The mixture was poured intowater (500 mL) and extracted with DCM (2 x 300 mL). The combined organic phaseswere washed with brine (2 x 500 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the title compound (25.74 g, 96 % yield, 96.7 % purity on LCMS) as a white solid.1H NMR (CDC13): 6 7.70 (d, 1 H), 7.15 (t, 1 H), 7.02 (d, 1 H), 2.95 (t, 2 H), 2.81 (t, 2 H),2.18 (s, 3 H) and 2.15-2.08 (m, 2 H).LCMS: m/z 176.2 (M+H)÷ (ESj.
91% In ethanol; at 20℃; for 1h; (1242) [00410] Into a 250-mL round-bottom flask was added 2,3-dihydro-l -inden-4-amine (5.00 g, 37.5 mmol) and ethanol (100 mL). Acetic anhydride (7.67 g, 7.10 mL, 75, 1 mmol) was added and the resulting solution was stirred for 1 h at RT. The reaction mixture was concentrated in vacuo and then diluted with ether (20 mL). The solid product was collected by filtration and dried in vacuo to afford A -(2,3-dihydro-lH-inden-4-yl)acetamide as an off-white solid (6.0 g, 91%). LCMS (ESI, m/z): i 76
66% In ethanol; at 0 - 20℃; for 15h; To a solution of 2,3-dihydro-lH-inden-4-amine (3.4 g, 26 mmol) in ethanol (45 mL) was added a solution of acetic anhydride (4.9 mL, 52 mmol) in ethanol (15 mL) dropwise at 0 C. The resulting mixture was gradually warmed up to RT and stirred for 15 h. Solvent was removed under reduced pressure and the residue was triturated with diethyl ether to afford titled compound as off white solid (3 g, 66%). LCMS [M+H]+= 176.3.
45% In ethanol; at 0 - 20℃; for 3h;Inert atmosphere; A solution of 2,3-dihydro-1 H-inden-4-amine, 1 (500 mg, 3.75 mmol) in EtOH (5 mL) was cooled to 0 C and treated dropwise with acetic anhydride (0.95 g, 9.37 mmol) under nitrogen atmosphere. The resulting reaction mixture was warmed to RT and stirred for 3h. Upon completion of reaction, (TLC, 30% ethyl acetate-hexanes, Rf, 0.2), the reaction mixture was concentrated in vacuo. The residue obtained was diluted with diethyl ether, filtered and dried in vacuo to give A/-(2,3-dihydro-1 /-/-inden-4-yl)acetamide (0.3 g, 45%) as a white solid.1H NMR (400 MHz, DMSO-afe): delta = 9.29 (s, 1 H), 7.41 (d, J = 8.0 Hz, 1 H), 7.08 (t, J = 7.6 Hz, 1 H), 6.99 (d, J = 6.8 Hz, 1 H), 2.87 (t, J = 7.2 Hz, 2H), 2.80 (t, J = 7.2 Hz, 2H), 2.04 (s, 3H), 1 .99-1 .95 (m, 2H). LCMS (m/z): 176.40 [M+H]+

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YieldReaction ConditionsOperation in experiment
90% With acetic anhydride; at 0℃; [0189] The <strong>[32202-61-2]indan-4-ylamine</strong> was dissolved in pure acetic anhydride at 0° C. The resulting precipitate which rapidly occurs was filtered and washed with watet The product was collected with a yield of 90percent (grey white solid) and was sufficiently pure for use at the following step without thrther purification.[0190] ?H NMR (CDC13) oe 7.73 (d, 1H, Har, J=8. 1); 7.15 (t, 1H, Har, J=8.1); 7.02 (d, 1H, Har, J=8.0); 6.96 (brs, 1H, NH);2.95 (t, 2H, CH2, J=7.5); 2.81 (t, 2H, CH2, J=7.4); 2.18 (s, 3H, CH3); 2.10 (qn, 2H, CH2, J=7.5).
 

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