36050-35-8|2-Methyl-3-nitrothiophene-5-carboxylic Acid| Ambeed

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CAS No. :	36050-35-8
Formula :	C₆H₅NO₄S
M.W :	187.17
SMILES Code :	O=C(C1=CC([N+]([O-])=O)=C(C)S1)O
MDL No. :	MFCD00507024

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Yield	Reaction Conditions	Operation in experiment
98%	With sulfuric acid; at 20℃;Heating / reflux;	Fuming nitric acid (3 eq.) was added dropwise to Ac2O (5 eq.) at -200C, then 5-methyl-2- thiophenecarboxylic acid (1 eq.) was added portion-wise and the mixture placed in an ice bath. After stirring at 00C for 1.5 h the reaction mixture was poured into ice, and when the ice was molten the precipitate was filtered off (66%). To a IM solution of the latter in MeOH, cone. H2SO4 (1.4 eq.) was added at RT. The mixture was stirred overnight at reflux. All volatiles were evaporated i. vac, then the residual material was mixed with water and the resulting solution extracted with EtOAc; the organic layer was washed with sat. NaHCO3 and brine, dried over Na2SO4 and concentrated (98%). 1H-NMR (400 MHz, CDCl3, 300K, δ) 8.21 (IH, s), 3.93 (s, 3H), 2.85 (s, 3H).
93%	With sulfuric acid; for 24.0h;Heating / reflux;	Compound 7.2 (10 g, 53.4 mmol, 1 equiv) in MeOH (100 niL) was treated with sulfuric acid (10 mL, 19 mmol, 3.5 equiv) and heated to reflux for 1 day. After the reaction mixture was cooled to ambient temperature, the solvent was evaporated. The residue was dissolved in EtOAc and quenched with saturated NaHCO3, then the layers were separated. The organic layer was washed with brine, dried (Na2SO4), filtered, concentrated, and dried in vacuo to yield 5-methyl-4-nitro-thiophene-2-carboxylic acid methyl ester 7.3 (9.95 g, 93%) as a pale-brown solid. MS: 202.00 (M+H+); 1H-NMR (DMSO-d6): £(ppm) 8.06 (s, IH), 3.84 (s, 3H), 2.78 (s, 3H).
69%	With sulfuric acid; In water; for 48.0h;Heating / reflux;	Example 1 : 6-CYCLOHEXYL-5-PHENYL-4H-THIENO [3, 2-B] PYRROLE-2- carboxylic acid; Step 1 : methyl 5-METHYL-4-NITROTHIOPHENE-2-CARBOXYLATE; A solution (0.5 M) of 5-methyl-4-nitrothiophene-2-carboxylic acid in methanol was treated with sulfuric acid (3.5 eq. ). The reaction mixture was heated to reflux for 48 h. After cooling down, solvent was evaporated giving a residue that was dissolved in AcOEt and water was added. The organic phase was separated and the aqueous layer was extracted with AcOEt. The combined organic phase was washed sequentially with aqueous NAHCO3 (saturated solution) and brine, then dried and concentrated giving the title compound (69%) as solid. 'H NMR (300 MHz, CDCl3, 300 K) 8 2.84 (s, 3H), 3.91 (s, 3H), 8.20 (s, 1H) ; MS (ES+) M/Z 202 (M+H) +.

66%	With sulfuric acid; for 16.0h;	To a solution of 5-methyl-4-nitrothiophene 2-carboxylic acid (7.6 g) in 150 mL of methanol was added 5 mL concentrated sulfuric acid. After stirring for 16h, the mixture was cooled on ice and neutralized with saturated sodium bicarbonate soluton. The product was extracted with ethyl acetate (Ix 50 ml). The separated organic layer was dried, filtered and concentrated, and passed through a silica gel plug, eluting with 50% ethyl acetate/hexanes. The filtrate was concentrated to give 5.4 g (66%) of 5-methyl-4- nitrothiophene 2-carboxylic acid methyl ester as a solid.
62%	With sulfuric acid; for 20.0h;Reflux;	The steps are:5-methyl-4-nitro - thiophene-2-carboxylic acid (4.0g, 21.37mmol) was dissolvedin methanol (40 mL), and Concentrated sulfuric acid (5mL), stirred at refluxfor 20 hours. Cooling to room temperature, methanol was distilled off underreduced pressure, to the residue was ethyl Acetate (200 mL) was dissolved,washed with water, and concentrated to give a brown oil methyl-4-nitro -thiophene-2-carboxylate (2.5 g, 62%).
	With sulfuric acid;Heating / reflux;	To nitric acid (specific gravity 1.42, 400 mL) cooled to -5C was dropwise added sulfuric acid (230 mL), and the mixture was stirred at -5C for 1 hr after the dropwise addition. 5-Methyl-thiophene-2-carboxylic acid (100 g) was added in small portions to the reaction mixture over 30 min. The reaction mixture was stirred for 1 hr, poured into ice and the precipitated crystals were collected by filtration. The crystals were washed with water and dried. The obtained crystals were dissolved in methanol (500 mL), sulfuric acid (100 mL) was added, and the mixture was heated under reflux overnight. The reaction mixture was concentrated, water was added, and the precipitated crystals were collected by filtration. The crystals were washed with water and dried to give methyl 5-methyl-4-nitrothiophene-2-carboxylate (95 g, yield 63%) as yellow crystals. melting point 81C.
15 g	With sulfuric acid;Reflux;	Step 1 : Methyl 5-methyl-4-nitrothiophene-2-carboxylate: A mixture of 5-methyl-4- nitrothiophene-2-carboxylic acid (15.9 g, 85.026 mmol) in dry methanol (160 ml) and sulfuric acid (2.8 ml) was refluxed overnight. The reaction mixture was cooled to room temperature, concentrated under reduced pressure and diluted with ice cold water (200 ml). The precipitated solid was collected by filtration and dried to yield 15 g of product as an off-white solid. 1H NMR (300 MHz, CDC13): δ 2.84 (s, 3H), 3.91 (s, 3H), 8.20 (s, 1H).

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CAS No.: 36050-35-8

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CAS No.: 36050-35-8

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Code	Phrase
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Prevention
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