3,3-DiMethyl-5-nitroindoline synthesis
- Product Name:3,3-DiMethyl-5-nitroindoline
- CAS Number:848047-43-8
- Molecular formula:C10H12N2O2
- Molecular Weight:192.21
116584-61-3
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Yield:848047-43-8 94%
Reaction Conditions:
with hydrogenchloride in water at 100; for 1 h;Inert atmosphere;
Steps:
3,3-Dimethyl-5-nitroindoline (8)
1-(3,3-Dimethyl-5-nitroindolin-1-yl)ethan-1-one (7, 2.70 g, 11.5 mmol) was added to20% HCl (50 mL), and the mixture was heated to 100 C. After 1 h, all of the solid haddissolved, indicating the reaction was complete. The mixture was poured into 1 MNaOH (150 mL). The aqueous mixture was extracted with EtOAc (375 mL). Thecombined organic layers were washed with aqueous NaCl (100 mL), dried (Na2SO4),and concentrated under vacuum to afford 8 (2.07 g, 94%) as a yellow solid, mp 74-76 C. IR: 3388, 1558, 1363 cm1; 1H NMR (400 MHz, CDCl3): d 8.03 (dd, J8.7,2.3 Hz, 1H), 7.90 (d, J2.3 Hz, 1H), 6.49 (d, J8.7 Hz, 1H), 4.45 (br s, 1H), 3.49 (s,2H), 1.35 (s, 6H); 13C NMR (100 MHz, CDCl3): d 155.9, 139.2, 138.2, 126.1, 118.9,106.6, 61.7, 41.1, 27.9; MS (EI): m/z 192 (M).Anal. Calcd for C10H12N2O2: C, 62.49: H, 6.29: N, 14.57. Found: C, 62.56; H, 6.31;N, 14.55.
References:
Berlin, K. Darrell;Bryant, Daniel J.;Bunce, Richard A. [Organic Preparations and Procedures International,2020,vol. 53,# 1,p. 68 - 77]
100511-00-0
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13296-94-1
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57045-86-0
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848047-41-6
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