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Structure of 5307-17-5

Chemical Structure| 5307-17-5

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Product Details of [ 5307-17-5 ]

CAS No. :5307-17-5
Formula : C9H9NO5
M.W : 211.17
SMILES Code : O=C(OC)C1=CC=CC(OC)=C1[N+]([O-])=O
MDL No. :MFCD00051968
InChI Key :FDQQRLPHAAICCR-UHFFFAOYSA-N
Pubchem ID :79195

Safety of [ 5307-17-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 5307-17-5 ]

* 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 [ 5307-17-5 ]

[ 5307-17-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 5307-17-5 ]
  • [ 5121-34-6 ]
YieldReaction ConditionsOperation in experiment
99% With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20℃; for 18h; A suspension of 10 methyl 3-methoxy-2-nitrobenzoate (26.2 g, 124 mmol) and 12 Pd/C (10 wt. %, 6.0 g) in 13 THF (400 mL) and MeOH (200 mL) was stirred under an atmosphere of H2 at room temperature for 18 hours. 14 EtOAc (300 mL) was added to the mixture and filtered through a Celite pad. The filtrate was concentrated in vacuo to provide the 15 title compound (22.4 g, 99%) as colorless oil. 1H NMR (400 MHz, CDCl3) delta 7.47 (dd, J=8.2, 1.2 Hz, 1H), 6.85 (dd, J=8.2, 1.2 Hz, 1H), 6.58 (t, J=8.2 Hz, 1H), 6.00 (brs, 2H), 3.87 (s, 3H); [M+H]+ 182.
95% With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 3102.97 Torr; for 2h; Step 3: Methyl 2-am5no-3-methoxybenzoateA mixture of methyl 3-methoxy-2-nitrobenzoate (27 g, 0.127 mol) and 10% Pd-C (13 g) in 500 mL of methanol was stirred at room temperature for 2 h at 60 PSI in a Parr hydrogenation apparatus. After confirming the completion of reaction by TLC, the reaction mixture was filtered through Celite reagent and the Celite reagent was washed with 20% MeOH in ethyl acetate (2 L). The filtrate was concentrated under reduced pressure and the solid obtained was dried under high vacuum to afford the title compound (22 g, 95%). H NMR (400 MHz, DMSO-d6) : delta 7.33 (dd, J' = 8.4 Hz, J" = 1.2 Hz, 1H), 6.97 (dd, J' = 7.6 Hz, J" = 0.8 Hz, 1H), 6.52 (t, J = 8.4 Hz, 1H), 6.32 (brs, 2H), 3.81 (s, 3H), 3.72 (s, 3H); ESI-MS : Calculated mass: 181.07; Observed mass: 182.0 [M + H]+.
With hydrogen;5%-palladium/activated carbon; In tetrahydrofuran; methanol; at 20℃; for 19.5h; Step 2; The crude product (23.90 g) obtained in Step 1 was suspended in a mixed solvent of tetrahydrofuran (150 ,ml) and methanol (50 ml), and 5% palladium-carbon (containing water) (2.30 g) was added. The mixture was stirred under a hydrogen atmosphere at room temperature for 19.5 hr. Ethyl acetate (200 ml) was added to the reaction mixture and filtered through celite. The filtrate was concentrated under reduced pressure and water was removed azeotropically with toluene to give a crude product (18.80 g) as a brown oil.
With hydrogen;5%-palladium/activated carbon; In tetrahydrofuran; methanol; at 20℃; for 19.5h; The crude product (23.90 g) obtained in Step 1 was suspended in a mixture of tetrahydrofuran (150 ml) and methanol (50 ml), and 5% palladium-carbon (wet)(2.30 g) was added. The mixture was stirred under a hydrogen atmosphere at room temperature for 19.5 hrs. Ethyl acetate (200 ml) was added to the reaction mixture and the mixture was filtered with Celite. The filtrate was concentrated under reduced pressure and the water was removed azeotropically with toluene to give a crude product (18.80 g) as a brown oil.
With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20℃; for 18h; A suspension of compound 52 (26.2 g, 124 mmol) and Pd/C (10 wt. %, 6.0 g) in THF (400 mL) and MeOH (200 mL) was stirred under an atmosphere of H2 at room temperature for 18 hours. EtOAc (300 mL) was added to the mixture and filtered through a Celite pad. The filtrate was concentrated in vacuo to provide the crude product 53 (22.4 g, 99%) as colorless oil.
86.7 g With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; methanol; at 20 - 40℃; for 48h; Reference Example 37 [Step a] To a mixed solution of compound 1 (100 g, 473 mmol) in tetrahydrofuran (630 mL) and methanol (210 mL) was added palladium/carbon (10 wt%, 10.0 g), and the mixture was stirred in a hydrogen atmosphere at room temperature for 29 hr. The mixture was further stirred with heating at 40C for 19 hr. The reaction solution was substituted with nitrogen, filtered through celite, and concentrated to give compound 2 (86.7 g). 1H-NMR (400 MHz, CDCl3)delta: 3.87(6H, s), 6.00(2H, brs), 6.57(1H, t, J=8.0Hz), 6.85(1H,dd, J=1.2, 8.0Hz), 7.47(1H, dd, J=1.2, 8.4Hz).

  • 2
  • [ 5307-17-5 ]
  • [ 17672-21-8 ]
  • 3
  • [ 5307-17-5 ]
  • [ 89942-77-8 ]
YieldReaction ConditionsOperation in experiment
98% With aluminum (III) chloride; In dichloromethane; Our next target was the synthesis of 2-aminophenol derivative 8, which was desirable for the construction of 4 (Scheme 5). Selective reduction of the carboxyl ester 11 by LiAlH4 in dry THF or NaBH4 in THF/MeOH gave 13 in up to 92-98% yield (Scheme 6). The deprotection of methoxyl group of 13 by AlCl3, however, gave 14 in only 61% yield, along with some unreacted 13. Although the deprotection of 13 by BBr3 also gave 14, the reaction mixture contained several unidentified by-products. Selective reduction of ester 12 by NaBH4 in THF/MeOH even did not proceed. We finally found 12 could be reduced by LiAlH4 in anhydrous THF to afford 14 in about 82% yield. Then the desirable 8 was prepared by hydrogenation catalyzed by Pd/C.
 

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