22768-05-4|Methyl 3-(3-nitrophenyl)propanoate| Ambeed

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Quality Control of [ 22768-05-4 ] Purity: 98% SDS Specification

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NMR

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Product Details of [ 22768-05-4 ]

CAS No. :	22768-05-4
Formula :	C₁₀H₁₁NO₄
M.W :	209.20
SMILES Code :	O=C(OC)CCC1=CC=CC([N+]([O-])=O)=C1
MDL No. :	MFCD22987434
InChI Key :	NOVBKWKVTOTPTB-UHFFFAOYSA-N
Pubchem ID :	11344816

Safety of [ 22768-05-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 22768-05-4 ]

* 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 [ 22768-05-4 ]

[ 22768-05-4 ] Synthesis Path-Downstream 1~16

1
[ 1664-59-1 ]
[ 22768-05-4 ]

References: [1]Tetrahedron Letters,1987,vol. 28,p. 1321 - 1322.

Yield	Reaction Conditions	Operation in experiment
		gaseous hydrochloric acid is bubbled for 3 hours through a solution of 5 g of (RS)-2-(3-nitrophenyl)propionitrile in 40 cm3 of methanol. The mixture obtained is stirred under reflux for 30 minutes, and the insoluble product is separated by filtration. The filtrate is concentrated to dryness under reduced pressure at 40 C. The crude product is purified by chromatography on silica [eluent:petroleum ether/ethyl acetate (80/20 by volume)]. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure at 40 C. 4 g of methyl (RS)-3-(3-nitrophenyl)propionate are thus obtained in the form of an oil used as it is in subsequent syntheses. (RS)-2-(3-Nitrophenyl)propionitrile may be prepared according to the method described by E. Felder et al., J. Med. Chem., 13, 559 (1970).

3
[ 500131-01-1 ]
[ 22768-05-4 ]
[ 63307-44-8 ]
1-methoxy-3-(3-nitro-phenyl)-propan-2-ol [ No CAS ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 1657 - 1660.

4
[ 67-56-1 ]
[ 1664-57-9 ]
[ 22768-05-4 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; at 60.0℃; for 2.0h;	To a solution of above product (1.0 eq) in MeOH (0.74 M) was added SOCb (2.0 eq) at RT. The resulting mixture was stirred at 60 C for 2 h. Then the mixture was cooled down to r.t, concentrated under reduced pressure. The residue was diluted withH20 (150 mL), and extracted with EtOAc (2x50 mL). The organic phase was washed with sat. aq NaHCOs (2x20 mL), dried over Na2S04, concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent: petroleum ether/EtOAc 10:1) to give the title compound as a white solid.
	With hydrogenchloride; at 60.0℃; for 1.0h;	A mixture of intermediate 1 (5 g, 25.62 mmol, 1 eq) and HCl/MeOH (50 mL) was heated to 60 C, and the mixture was stirred at 60 C for 1 h. The reaction was monitored by LCMS and when omplete, the reaction mixture was concentrated in vacuo to yield intermediate 2 (5.3 g, crude) was obtained as a white solid. LCMS: m/z = 210.1 (M+H+), 1H-NMR: (400 MHz, DMSO-de) δ 8.10 (s, 1 H) 8.05 (dd, >8.13, 1.65 Hz, 1 H) 7.71 (d, >7.58 Hz, 1 H) 7.53 - 7.61 (m, 1 H) 3.57 s, 3 H) 2.94- 3.03 (m, 2 H) 2.66 - 2.75 (m, 2 H).
	With hydrogenchloride; at 60.0℃; for 1.0h;	A mixture of intermediate 1 (5 g, 25.62 mmol, 1 eq) and HCl/MeOH (50 mL) was heated to 60 C, and the mixture was stirred at 60 C for 1 h. The reaction was monitored by LCMS and when omplete, the reaction mixture was concentrated in vacuo to yield intermediate 2 (5.3 g, crude) was obtained as a white solid. LCMS: m/z = 210.1 (M+H+), 1H-NMR: (400 MHz, DMSO-de) δ 8.10 (s, 1 H) 8.05 (dd, >8.13, 1.65 Hz, 1 H) 7.71 (d, >7.58 Hz, 1 H) 7.53 - 7.61 (m, 1 H) 3.57 s, 3 H) 2.94- 3.03 (m, 2 H) 2.66 - 2.75 (m, 2 H).

References: [1]Patent: WO2020/139636,2020,A1 .Location in patent: Paragraph 00285-00286.
[2]Patent: WO2021/257754,2021,A1 .Location in patent: Page/Page column 243.
[3]Patent: WO2021/257754,2021,A1 .Location in patent: Page/Page column 243.

5
[ 22768-05-4 ]
[ 35418-08-7 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium 10% on activated carbon; hydrogen; In methanol; at 20.0℃; for 16.0h;	To a stirring solution of above product (1.0 eq) in MeOH (0.5 M) was added Pd/C (10%wt), and the mixture was stirred under H2 for 16 h at RT. The solid was filtered off, and filtrate was concentrated. The residue was dissolved in DCM (30 mL), and treated with 4.0 M HCl/dioxane (9 mL). The mixture was concentrated, and the residue was triturated withEt20 (30 mL). The solid was collected by filtration, and then dissolved in H2O (100 mL). The solution was adjusted to pH about 9 with sat. aq NaHCOs and extracted with DCM (2x50 mL). The DCM layer was dried over Na2S04, concentrated under reduced pressure to give the title compound as a slightly yellow oil. LC-MS (m/z): [M+l]+ = 180.
	With iron(0); ammonia hydrochloride; In ethanol; water monomer; at 90.0℃; for 2.0h;Inert atmosphere;	To a solution of intermediate 2 (4.3 g, 20.55 mmol, 1 eq) in EtOH (40 mL) and H2O (15 mL) was added NH4CI (5.43 g, 102.77 mmol, 5 eq) and the reaction was heated to 90 C, then Fe (5.74 g, 102.77 mmol, 5 eq) was added, the mixture was stirred at 90 C for 2 h under N2 atmosphere. The reaction was monitored by LCMS and when complete, the reaction mixture was filtered and concentrated in vacuo to yield intermediate 3 (3.7 g, crude) was obtained as a yellow olid. LCMS: m/z = 180.2 (M+H+), -ΝΜΚ: (400 MHz, DMSO -ck) δ = 6.91 (t, >7.52 Hz, 1 H) 6.28 - 6.44 (m, 3 H) 4.94 (s, 2 H) 3.58 (s, 3 H) 2.63 - 2.74 (m, 2 H) 2.52 - 2.59 (m, 2 H).
	With iron(0); ammonia hydrochloride; In ethanol; water monomer; at 90.0℃; for 2.0h;Inert atmosphere;	To a solution of intermediate 2 (4.3 g, 20.55 mmol, 1 eq) in EtOH (40 mL) and H2O (15 mL) was added NH4CI (5.43 g, 102.77 mmol, 5 eq) and the reaction was heated to 90 C, then Fe (5.74 g, 102.77 mmol, 5 eq) was added, the mixture was stirred at 90 C for 2 h under N2 atmosphere. The reaction was monitored by LCMS and when complete, the reaction mixture was filtered and concentrated in vacuo to yield intermediate 3 (3.7 g, crude) was obtained as a yellow olid. LCMS: m/z = 180.2 (M+H+), -ΝΜΚ: (400 MHz, DMSO -ck) δ = 6.91 (t, >7.52 Hz, 1 H) 6.28 - 6.44 (m, 3 H) 4.94 (s, 2 H) 3.58 (s, 3 H) 2.63 - 2.74 (m, 2 H) 2.52 - 2.59 (m, 2 H).

References: [1]Patent: WO2020/139636,2020,A1 .Location in patent: Paragraph 00287-00288.
[2]Patent: WO2021/257754,2021,A1 .Location in patent: Page/Page column 243-244.
[3]Patent: WO2021/257754,2021,A1 .Location in patent: Page/Page column 243-244.

6
[ 22768-05-4 ]
methyl 3-(3-((4-((5,6-dimethyl-[2,2'-bipyridin]-3-yl)oxy)pyridin-2-yl)amino)phenyl)propanoate [ No CAS ]

References: [1]Patent: WO2020/139636,2020,A1 .

7
[ 22768-05-4 ]
3-(3-((4-((5,6-dimethyl-[2,2'-bipyridin]-3-yl)oxy)pyridin-2-yl)amino)phenyl)propanoic acid formic acid salt [ No CAS ]

References: [1]Patent: WO2020/139636,2020,A1 .

8
[ 99-61-6 ]
[ 22768-05-4 ]