[ CAS No. 2199-49-7 ]

Name: Ethyl 4-methyl-1H-pyrrole-3-carboxylate
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SKU: A261744
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Product Details of [ 2199-49-7 ]

CAS No. :	2199-49-7	MDL No. :	MFCD00030417
Formula :	C₈H₁₁NO₂	Boiling Point :	289.7°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	MMDOYVVZUVZLHQ-UHFFFAOYSA-N
M.W :	153.18	Pubchem ID :	235044
Synonyms :

Computed Properties of [ 2199-49-7 ]

TPSA :Topological Polar Surface Area	42.1	H-Bond Acceptor Count :	2
XLogP3 :	-	H-Bond Donor Count :	1
SP3 :	0.38	Rotatable Bond Count :	3

Safety of [ 2199-49-7 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2199-49-7 ]

Downstream synthetic route of [ 2199-49-7 ]

[ 2199-49-7 ] Synthesis Path-Downstream 1~10

1
[ 2199-49-7 ]
[4-(11-bromo-undecyloxy)-phenyl]-(4-methoxy-phenyl)-diazene [ No CAS ]
N-{11-[4-(4'-methoxyphenylazo)phenyloxy]undecyl}-3-methylpyrrole-4-carboxylate ethyl ester [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2002,vol. 12,p. 579 - 585

2
[ 2199-49-7 ]
[ 6339-66-8 ]

Yield	Reaction Conditions	Operation in experiment
3.3g (46%)	With trichlorophosphate; In sodium hydroxide; N,N-dimethyl-formamide;	Step 2 Preparation of 5-Formyl-<strong>[2199-49-7]4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester</strong> POCl3 (4 mL, 1.1 eq) added to 9 mL (3 eq) of DMF cooled in an ice bath. After 15 mins, a solution of the <strong>[2199-49-7]4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester</strong> (6 g, 39.2 mmol) in DMF (2M, 20 mL) was added to the reaction and stirring continued at rt. After 2 hr, the reaction mixture was diluted with water (100 mL) and basified to pH=1 1 with IN NaOH. The aqueous layer was extracted into DCM (2250 mL), washing the combined organic layers with water (2400 mL), dried (MgSO4), filtered through a plug of silica and concentrated to afford a pinkish solid. Trituration with hexanes afforded 3.3g (46%) of 5-formyl-<strong>[2199-49-7]4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester</strong> as a tan solid 1H NMR (300 MHz, DMSO-d6) delta 12.4 (br s, 1H, NH), 9.69 (s, 1H, CHO), 7.59 (s, 1H), 4.16 (q, J =6.8 Hz, 2H, OCH2CH3), 2.48 (s, 3H, CH3), 1.24 (t, J=6.8 Hz, 3H, OCH2CH3). MS m/z 181 [M+].
3.3 g (46%)	With trichlorophosphate; In N,N-dimethyl-formamide;	(Lit. ref.: Cheng et al., J. Heterocyclic Chem., 1976, 13, 1145-1147). POCl3 (4 mL, 1.1 eq) added to 9 mL (3 eq) of DMF cooled in an ice bath. After 15 mins, a solution of the <strong>[2199-49-7]4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester</strong> (6 g, 39.2 mmol) in DMF (2M, 20 mL) was added to the reaction and stirring continued at rt. After 2 hr, the reaction mixture was diluted with water (100 mL) and basified to pH=11 with 1N NaOH. The aqueous layer was extracted into DCM (2250 mL), washing the combined organic layers with water (2400 mL), dried (MgSO4), filtered through a plug of silica and concentrated to afford a pinkish solid. Trituration with hexanes afforded 3.3 g (46%) of 5-formyl-<strong>[2199-49-7]4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester</strong> as a tan solid 1H NMR (300 MHz, DMSO-d6) delta 12.4 (br s, 1H, NH), 9.69 (s, 1H, CHO), 7.59 (s, 1H), 4.16 (q, J=6.8 Hz, 2H, OC2CH3), 2.48 (s, 3H, CH3), 1.24 (t, J=6.8 Hz, 3H, OCH2CH3). MS m/z 181 [M+].

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 2089,2093
[2]Journal of the American Chemical Society,1953,vol. 75,p. 2089,2093
[3]Patent: US2003/69297,2003,A1
[4]Patent: US2003/125370,2003,A1

3
[ 2199-49-7 ]
2,5-dibromo-4-methyl-pyrrole-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 2089,2093

4
[ 2199-49-7 ]
[ 874496-31-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide;	Reference Example 46 Ethyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate Using <strong>[2199-49-7]ethyl 4-methyl-1H-pyrrole-3-carboxylate</strong> (4.50 g) and N-bromosuccinimide (5.2 g), a procedure as in Reference Example 40 was performed to give the title compound as a pale-yellow solid (yield 5.20 g, 76%). 1H-NMR (CDCl3)delta: 1.34 (3H, t, J=7.4 Hz), 2.23 (3H, s), 4.27 (2H, q, J=7.4 Hz), 7.38 (1H, d, J=3.0 Hz), 8.30 (1H, brs).

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 2089,2093
[2]Patent: EP1803709,2007,A1

5
[ 2199-49-7 ]
[ 64276-66-0 ]

Reference： [1]Gazzetta Chimica Italiana,1955,vol. 85,p. 1378,1392
Annali di Chimica (Rome, Italy),1956,vol. 46,p. 847,855

6
[ 2199-49-7 ]
[ 856289-32-2 ]
3-[5-(4-ethoxycarbonyl-3-methyl-pyrrol-2-ylmethylene)-2-bromo-4-methyl-5<i>H</i>-pyrrol-3-yl]-propionic acid ; hydrobromide [ No CAS ]

Reference： [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1935,vol. 231,p. 231,252

7
[ 5448-13-5 ]
[ 2199-49-7 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 5295,5297
[2]Chemische Berichte,1957,vol. 90,p. 79,81

8
4-methyl-pyrrole-dicarboxylic acid-(2.3)-ethyl ester-⁽³⁾ [ No CAS ]
[ 2199-49-7 ]

Reference： [1]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1926,vol. 155,p. 61

Yield	Reaction Conditions	Operation in experiment
71%	With potassium tert-butylate; In tetrahydrofuran; at 10 - 35℃; for 1.5h;	General procedure: Reference Example 39 Methyl 1H-pyrrole-3-carboxylate A solution (250 mL) of p-toluenesulfonylmethyl isocyanide (15.0 g) and methyl acrylate (6.92 mL) in tetrahydrofuran was added dropwise to a suspension (100 mL) of potassium tert-butoxide in tetrahydrofuran over 30 min. The reaction mixture was stirred at room temperature for 1 hr, and filtered through a glass filter filled with silica gel (diameter 8 cm, height 4 cm), and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1?2:1) to give the title compound as a pale-yellow solid (yield 4.69 g, 49%). 1H-NMR (CDCl3)delta: 3.82 (3H, s), 6.15 (1H, m), 6.75 (1H, m), 7.43 (1H, m), 8.50 (1H, brs).
6g (78%)		Step 1 Preparation of 4-Methyl-1H-pyrrole-3-carboxylic acid ethyl ester To a suspension of sodium hydride (4 g of 60% dispersion, 2eq, washed with diethyl ether) in diethyl ether (200 mL), cooled in an ice bath with stirring was added slowly a solution of ethyl crotonate (6.2 mL, 50 mmol) and p-tosylmethyl isocyanide (9.7 g, 50 mmol) in 80 mL of DMSO and 160 mL diethyl ether. Upon complete addition of the solution, the reaction mixture was stirred at room temperature for 1 hr. The reaction was quenched with 400 mL water and extracted into diethyl ether (2*100 mL), dried (MgSO4) and concentrated to afford 6g (78%) of <strong>[2199-49-7]4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester</strong> as a brown oil which solidified upon standing. 1H NMR (300 MHz, DMSO-d6) delta 11.1 (br s, 1H, NH), 9.78 (t, J=2.7 Hz, 1H), 6.56 (s, 1H), 4.12 (q, J=7.2 Hz, 2H, OCH2CH3), 2.15 (s, 3H, CH3), 1.22 (t, J=7.2 Hz, 3H, OCH2CH3). MS m/z 153 [M+].
6 g (78%)		Example 3 Synthesis of 5-formyl-4-methyl-1H-pyrrole-3-carboxylic acid (Pyrrole Aldehyde-9) To a suspension of sodium hydride (4 g of 60% dispersion, 2eq, washed with diethyl ether) in diethyl ether (200 mL), cooled in an ice bath with stirring was added slowly a solution of ethyl crotonate (6.2 mL, 50 mmol) and p-tosylmethyl isocyanide (9.7 g, 50 mmol) in 80 mL of DMSO and 160 mL diethyl ether. Upon complete addition of the solution, the reaction mixture was stirred at room temperature for 1 hr. The reaction was quenched with 400 mL water and extracted into diethyl ether (2*100 mL), dried (MgSO4) and concentrated to afford 6 g (78%) of <strong>[2199-49-7]4-methyl-1H-pyrrole-3-carboxylic acid ethyl ester</strong> as a brown oil which solidified upon standing. 1H NMR (300 MHz, DMSO-d6) delta 11.1 (br s, 1H, NH), 9.78 (t, J=2.7 Hz, 1H), 6.56 (s, 1H), 4.12 (q, J=7.2 Hz, 2H, OCH2CH3), 2.15 (s, 3H, CH3), 1.22 (t, J=7.2 Hz, 3H, OCH2CH3). MS m/z 153 [M+].

		EXAMPLE 88 Ethyl 4-Methylpyrrole-3-carboxylate Ethyl 4-methylpyrrole-3-carboxylate was prepared according to the procedure of Cheng et al. [J. Heterocyclic Chem. 13, 1145 (1976)].
		Reference Example 45 Ethyl 4-methyl-1H-pyrrole-3-carboxylate Using p-toluenesulfonylmethyl isocyanide (8.55 g), ethyl crotonate (5.0 g) and potassium tert-butoxide (5.90 g), a procedure as in Reference Example 39 was performed to give the title compound as a pale-yellow solid (yield 4.77 g, 71%). 1H-NMR (CDCl3)delta: 1.34 (3H, t, J=6.8 Hz), 2.29 (3H, s), 4.27 (2H, q, J=6.8 Hz), 6.53 (1H, m), 7.38 (1H, m), 8.30 (1H, brs).
12.38 g (80%)		Ethyl 4-methylpyrrol-3-carboxylate. A solution of 11.86 g (0.1 moles) of ethyl crotonate and 19.50 g (0.1 moles) of p-toluenesulfonylmethylisocyanide in 500 mL of a 2:1 ether/dimethylsulfoxide was added dropwise into a suspension of 6.8 g of sodium hydride (60% mineral oil dispension, 0.17 moles) in ether at room temperature. Upon completion of addition the reaction mixture was stirred for 30 min and dilute with 400 mL of water. The aqueous layer was extracted with 3*100 mL of ether. The combined ether extracts were passed through a column of alumina eluding with dichloromethane. The organic solvent was evaporated and the resulting residue was solidified on standing. The solid was washed with hexane and dried at 40 C. in vacuum oven overnight to yield 12.38 g (80%) of the title compound.

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[ CAS No. 2199-49-7 ]

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[ 2199-49-7 ] Synthesis Path-Downstream 1~10

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Esters

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Aromatic Heterocycles

Pyrroles

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