2001-32-3|3-(2-Nitrophenyl)propanoic acid| Ambeed

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Quality Control of [ 2001-32-3 ] Purity: 95% SDS Specification

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Surveying the scope of aromatic decarboxylations catalyzed by prenylated-flavin dependent enzymes

Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto ; Prathamesh M. Datar ; Daniel J. DiRocco ; Katherine Huntera and E. Neil G. Marsh

DOI: 10.1039/D4FD00006D PubMed ID: 38837123 Faraday Discuss.,2024,252,208-222.

Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ∼35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.

Purchased from AmBeed: 27916-43-4 ; 2438-05-3 ; 501-89-3 ; 42287-94-5 ; 776-79-4 ; 53473-36-2 ; 7251-61-8 ; 42287-97-8 ; 1621-91-6 ; 37718-11-9 ; 288-13-1 ; 86-73-7 ; 104-53-0 ; 2018-90-8 ; 87-66-1 ; 135-19-3 ; 1664-57-9 ; 289-80-5 ; 693-95-8 ; 55-22-1 ; 102-93-2 ; 1477-50-5 ; 1632-76-4 ; 4780-79-4 ; 16642-79-8 ; 3581-89-3 ; 501-97-3 ; 771-50-6 ; 98-98-6 ; 619-64-7 ; 100-51-6 ; 402-45-9 ; 59-67-6 ; 93-60-7 ; 273-53-0 ; 2084-13-1 ; 51-17-2 ; 2459-09-8 ; 2459-07-6 ; 95-16-9 ; 459-31-4 ; 90-05-1 ; 150-76-5 ; 103-25-3 ; 271-44-3 ; 6293-56-7 ; 2550-26-7 ; 288-32-4 ; 501-52-0 ; 2001-32-3 ; 1592-38-7 ; 95-15-8 ; 91-19-0 ; 1122-61-8 ; 3724-19-4 ; 20173-24-4 ; 118-31-0 ; 6125-24-2 ; 60-12-8 ; 90-15-3 ; 120-72-9 ; 822-36-6 ; 288-47-1 ; 288-42-6 ; 2038-57-5 ; 38628-51-2 ; 1929-29-9 ; 15009-91-3 ; 1505-50-6 ; 581-40-8 ; 616-47-7 ; 1571-33-1

Product Details of [ 2001-32-3 ]

CAS No. :	2001-32-3
Formula :	C₉H₉NO₄
M.W :	195.17
SMILES Code :	O=C(O)CCC1=CC=CC=C1[N+]([O-])=O
MDL No. :	MFCD00130002
Boiling Point :	No data available
InChI Key :	OARKUZWAGHQLSL-UHFFFAOYSA-N
Pubchem ID :	74818

Safety of [ 2001-32-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 2001-32-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	4
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	51.62
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	83.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.09
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.54
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.61
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.89
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.25
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.97

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.07
Solubility	1.65 mg/ml ; 0.00844 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.89
Solubility	0.249 mg/ml ; 0.00127 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.97
Solubility	2.12 mg/ml ; 0.0108 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.4 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.73

Application In Synthesis of [ 2001-32-3 ]

* 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 [ 2001-32-3 ]

[ 2001-32-3 ] Synthesis Path-Downstream 1~35

1
[ 16793-89-8 ]
[ 151-50-8 ]
[ 2001-32-3 ]

References: [1]Collection of Czechoslovak Chemical Communications,1958,vol. 23,p. 1902,1907.

2
[ 2001-32-3 ]
[ 553-03-7 ]

References: [1]Zeitschrift fur Chemie,1869,p. 194.
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1693 - 1698.

3
[ 2001-32-3 ]
[ 33100-15-1 ]

References: [1]Journal of the American Chemical Society,1949,vol. 71,p. 2137,2138,2140.

4
[ 2001-32-3 ]
[ 18910-10-6 ]

References: [1]Chemische Berichte,1923,vol. 56,p. 2450.

5
[ 683215-25-0 ]
[ 2001-32-3 ]

References: [1]Chemische Berichte,1923,vol. 56,p. 2450.
[2]Chemische Berichte,1923,vol. 56,p. 2450.

6
[ 501-52-0 ]
[ 16642-79-8 ]
[ 2001-32-3 ]

References: [1]Chemische Berichte,1879,vol. 12,p. 600.
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2004,vol. 179,p. 221 - 226.
[3]Tetrahedron Letters,2005,vol. 46,p. 8307 - 8310.

7
[ 2001-32-3 ]
[ 85397-21-3 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In dichloromethane; for 2h;Heating / reflux;	A solution of 3- (2-nitrophenyl) propanoic acid (1.20 g, 6.15 mmol) and thionyl chloride (0. 878 g, 7. 38 mmol) in dichloromethane (5 ml) was stirred and heated to reflux for 2 hours. The mixture was concentrated under reduced pressure to obtain 3- (2-nitrophenyl) propanoyl chloride. To the obtained crude 3- (2-nitrophenyl) propanoyl chloride (1.31 g, 6.15 mmol) was added CS2, and alu- minum trichloride (1. 07 g, 8.0 mmol) was added portionwise at 0 C. The mixture was stirred at 70 C for 3 hours, and after cooled to ambient temperature, water was added and extracted with ethyl acetate. The organic layer was dried over MgS04, filtered, and concentrated under reduced pres- sure. The obtained residue was purified by silica gel column chromatography (hexane: ethylacetate 10: 1) to afford 4-nitroindan-1-one (0.44 g). 'H NMR (CDC13) 8 2.79-2. 82 (m, 2H), 3.64-3. 66 (m, 2H), 7.62 (t, J= 7.9 Hz, 1H), 8. 09 (d, J= 7.6 Hz, 1H), 8.47 (d, J= 8.2 Hz, 1H).
	With thionyl chloride;N,N-dimethyl-formamide; In dichloromethane; for 3h;Reflux;	In a single necked round-bottomed flask (100 mL), step-b product (5.8 g, 0.029 mol) was taken followed by dichloromethane (33 mL) and catalytic amount of dimethylformamide (0.1 mL). Thionyl chloride (2.2 mL) was added to it slowly. The reaction mixture was refluxed for 3 hours. The reaction mixture was concentrated under reduced pressure and thionyl chloride was removed by benzene (3 x 50 mL). The crude compound was directly taken for the next step without further purification (5.4 g).
	With thionyl chloride; In dichloromethane; for 2h;Heating / reflux;	To a solution of 2-nitrobenzyl bromide (1.00 g, 4.63 mmol) and diethyl malonate (0.741 g, 4.63 mmol) in 30 ml of hexane was added potassium carbonate (0.640 g, 4.63 mmol) and 18- Crown-6 (0.012 g, 0.05 mmol). After stirred at 80 C for 18 hours, the mixture was diluted with water and was extracted with ethyl acetate. The organic layer was washed with water, then with brine, and concentrated under reduced pressure to obtain crude diethyl (2-nitrobenzyl) malonate. A solution of crude diethyl (2-nitrobenzyl) malonate in 6N aqueous HC1 (15 ml) and acetic acid (15 ml) was stirred at refluxing temperature for 48 hours. After cooled to ambient temperature, the mixture was concentrated under reduced pressure. To the residue was added 10% aqueous NaOH solution and washed with ethyl acetate. The aqueous layer was acidified with aqueous HCl solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over MgS04, filtered, and concentrated under reduced pressure to obtain 3- (2-nitrophenyl) propanoic acid. 'H NMR (CDC13) 8 2.79 (t, J= 7.6 Hz, 2H), 3.24 (t, J= 7.6 Hz, 2H), 7. 38-7. 44 (m, 2H), 7.55 (dt, J= 7.6, 1.6 Hz, 1H), 7.96 (dd, J= 7.6, 1.6 Hz, 1H). A solution of 3- (2-nitrophenyl) propanoic acid (1.20 g, 6.15 mmol) and thionyl chloride (0. 878 g, 7.38 mmol) in dichloromethane (5 ml) was stirred and heated to reflux for 2 hours. The mixture was concentrated under reduced pressure to obtain 3- (2-nitrophenyl) propanoyl chloride. To the obtained crude 3- (2-nitrophenyl) propanoyl chloride (1.31 g, 6.15 mmol) was added CS2, and aluminum trichloride (1.07 g, 8. 0 mmol) was added portionwise at 0C. The mixture was stirred at 70C for 3 hours, and after cooled to ambient temperature, water was added and extracted with ethyl acetate. The organic layer was dried over MgS04, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane : ethylacetate 10: 1) to afford 4-nitroindan-1-one (0.44 g). 'H NMR (CDC13) 8 2.79-2. 82 (m, 2H), 3.64-3. 66 (m, 2H), 7.62 (t, J= 7.9 Hz, 1H), 8.09 (d, J= 7.6 Hz, 1H), 8.47 (d, J= 8.2 Hz, 1H). To a solution of 4-nitroindan-1-one (0.381 g, 2.15 mmol) in ethanol (5 ml) was added sodium borohydride (0.048 g, 1.29 mmol) at 0 C, and the mixture was stirred at room temperature for 3 hours. Aqueous solution of ammonium chloride was added to the mixture, and extracted with ethyl acetate. The organic layer was dried over MgS04, filtered, and concentrated under reduced pressure to obtain 4-nitroindan-1-ol. 'H NMR (CDC13) 8 1.90 (d, J= 6. 5 Hz, 1H), 2.00-2. 07 (m, 1H), 2.56-2. 63 (m, 1H), 3.25-3. 33 (m, 1H), 3.54-3. 60 (m, 1H), 5. 30-5. 35 (m, 1H), 7.44 (t, J= 8.2 Hz, 1H), 7.72 (d, J = 7.6 Hz, 1H), 8. 12 (d, J= 8. 2 Hz, 1H). A solution of 4-nitroindan-1-ol (0.385 g, 2.15 mmol) and p-toluenesulfonic acid (5. 0 mg, 0.03 mmol) in toluene (30 ml) was stirred and heated to reflux for 16 hours. After cooled to ambient temperature, the mixture was washed with aqueous sodium bicarbonate solution. The organic layer was dried over MgS04, filtered, and concentrated under reduced pressure. The obtained residue was purified by preparatory TLC (hexane: ethylacetate 3: 1) to afford 7-nitro-lH- indene (0.289 g). 'H NMR (CDC13) 8 3.94 (s, 2H), 6.75 (dt, J= 5. 7,1. 9 Hz, 1H), 6.93 (dt, J= 5. 7,1. 6 Hz, 1H), 7.45 (t, J= 8. 2 Hz, 1H), 7.68 (d, J= 7.6 Hz, 1H), 8. 05 (d, J= 8.2 Hz, 1H). To a solution of 2, 3-dimethyl-2-butene (21.5 mg, 0.31 mmol) in THF (2 ml) at 0C was added borane-THF (0.307 ml, 0.31 mmol) dropwise. After stirred for lhour at 0C, 7-nitro-1H-indene (45.0 mg, 0.28 mmol) in THF (5 ml) was added dropwise, and the mixture was stirred for 2 hours at ambient temperature. The mixture was cooled to 0C, and water (0.15 ml), 4N aqueous sodium hydroxide (0.45 ml), and 30% H202 (0. 45ml) were added. The mixture was then warmed to room temperature and poured into water, extracted with ethyl acetate and washed with brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. To the obtained mixture in toluene (1 ml) was added acetic anhydride (40.8 mg, 0.40 mmol) and pyridine (0.4 ml), and then stirred for 16 hours at room temperature. The mixture was concentrated under reduced pressure, and the obtained residue was purified by preparatory TLC (hexane: ethylacetate 2: 1) to obtain 4-nitro-2, 3-dihydro-lH-inden-2-yl acetate (16.0 mg). 'H NMR (CDC13) 8 2.03 (s, 3H), 3.12 (dd, J= 17. 5,1. 6 Hz, 1H), 3.40 (dd, J= 17. 5, 6. 3 Hz, 1H), 3.60 (dd, J= 19. 2,2. 2 Hz, 1H), 3.74 (dd, J= 19. 2,6. 6 Hz, 1H), 5.58-5. 62 (m, 1H), 7.39 (t, J= 7.9 Hz, 1H), 7.54 (d, J = 7.3 Hz, 1H), 8.06 (d, J = 8.2 Hz, 1H). To a mixture of 4-nitro-2, 3-dihydro-lH-inden-2-yl acetate (100 mg, 0.45 mmol) and ammonium chloride (100 mg) in ethanol (6 ml) and water (3 ml) was added iron powder (300 mg) portionwise at room temperature. The mixture was stirred at 90 C for 1 hour, and after cooled to room temperature, the mixture was dil...

References: [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 371 - 380.
[2]Patent: WO2005/40119,2005,A1 .Location in patent: Page/Page column 48-49.
[3]Journal of Organic Chemistry,2008,vol. 73,p. 2096 - 2104.
[4]Patent: WO2010/127855,2010,A1 .Location in patent: Page/Page column 145; 146.
[5]Patent: WO2005/40100,2005,A1 .Location in patent: Page/Page column 75-77.

8
[ 67-56-1 ]
[ 2001-32-3 ]
[ 1664-65-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 3889 - 3899.
[2]Helvetica Chimica Acta,1961,vol. 44,p. 1736 - 1747.

9
[ 2001-32-3 ]
[ 24623-25-4 ]

References: [1]Helvetica Chimica Acta,1961,vol. 44,p. 1736 - 1747.
[2]Patent: WO2005/40100,2005,A1 .

10
[ 612-23-7 ]
[ 105-53-3 ]
[ 2001-32-3 ]

References: [1]Helvetica Chimica Acta,1961,vol. 44,p. 1736 - 1747.

11
[ 501-52-0 ]
[ 16642-79-8 ]
[ 1664-57-9 ]
[ 2001-32-3 ]

References: [1]Journal of Organic Chemistry,1998,vol. 63,p. 952 - 958.

12
[ 7697-37-2 ]
[ 501-52-0 ]
[ 16642-79-8 ]
[ 2001-32-3 ]

References: [1]Chemische Berichte,1879,vol. 12,p. 600.

13
[ 7647-01-0 ]
[ 59803-35-9 ]
[ 2001-32-3 ]

References: [1]Chemische Berichte,1896,vol. 29,p. 636.
Chemische Berichte,1894,vol. 27,p. 2250.

14
HCl-salt 2-nitro-4-amino-hydrocinnamic acid [ No CAS ]
[ 66757-87-7 ]
[ 2001-32-3 ]

References: [1]Chemische Berichte,1880,vol. 13,p. 1680.

16
[ 7647-01-0 ]
[ 2001-32-3 ]
tin [ No CAS ]
[ 553-03-7 ]

References: [1]Chemische Berichte,1880,vol. 13,p. 1680.

Yield	Reaction Conditions	Operation in experiment
		B. Preparation of 3-(2-nitrophenyl)propionic acid (Compound B, Schema 1) The 164.2 g of oil containing diethyl (2-nitrophenylmethyl)-1,3-propanedioate, from Step A, was combined with 1 L of acetic acid and 1 L of aqueous 20% hydrochloric acid, and heated under reflux for 16 hours. The reaction mixture was cooled to ambient temperature, and concentrated under reduced pressure to give a residue. The residue was stirred with 450 mL of water, then 450 mL of aqueous 10% sodium hydroxide solution was added. The mixture was stirred for one hour, then was extracted with four portions of 450 mL each of diethyl ether. The organic layer was discarded. The aqueous layer was acidified with hydrochloric acid, and extracted with three portions of 300 mL each of diethyl ether. The combined extracts were dried with sodium sulfate, filtered, and the filtrate concentrated under reduced pressure to give a solid residue. The solid was dissolved with heating in 200 mL of toluene, and the solution was stirred for 16 hours while cooling to ambient temperature. The resultant slurry was further cooled to 10 C., and the solid collected by filtration. The solid was washed with pentane to give 74.2 g of 3-(2-nitrophenyl)propionic acid, m.p. 111-112 C.
		B. Preparation of 3-(2-nitrophenyl)propionic acid (Compound B, Schema 1) The 164.2 g of oil containing diethyl (2-nitrophenylmethyl)-1,3-propanedioate, from Step A, was combined with 1 L of acetic acid and 1 L of aqueous 20% hydrochloric acid, and heated under reflux for 16 hours. The reaction mixture was cooled to ambient temperature, and concentrated under reduced pressure to give a residue. The residue was stirred with 450 mL of water, then 450 mL of aqueous 10% sodium hydroxide solution was added. The mixture was stirred for one hour, then was extracted with four portions of 450 mL each of diethyl ether. The organic layer was discarded. The aqueous layer was acidified with hydrochloric acid, and extracted with three portions of 300 mL each of diethyl ether. The combined extracts were dried with sodium sulfate, filtered, and the filtrate concentrated under reduced pressure to give a solid residue. The solid was dissolved with heating in 200 mL of toluene, and the solution was stirred for 16 hours while cooling to ambient temperature. The resultant slurry was further cooled to 10 C., and the solid collected by filtration. The solid was washed with pentane to give 74.2 g of 3-(2-nitrophenyl)propionic acid, m.p. 111-112 C.

18
2-nitro-benzylmalonic acid diethyl ester [ No CAS ]
[ 2001-32-3 ]

References: [1]Chemische Berichte,1896,vol. 29,p. 636.
Chemische Berichte,1894,vol. 27,p. 2250.

19
HCl-salt 2-nitro-4-amino-hydrocinnamic acid [ No CAS ]
[ 2001-32-3 ]

References: [1]Chemische Berichte,1880,vol. 13,p. 1680.

20
[ 2001-32-3 ]
[ 7726-95-6 ]
red phosphorus [ No CAS ]
[ 18910-10-6 ]

References: [1]Chemische Berichte,1923,vol. 56,p. 2450.

21
[ 114304-24-4 ]
[ 2001-32-3 ]