14470-51-0|5,6-Dihydrothieno[2,3-c]pyridin-7(4H)-one| Ambeed

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CAS No. :	14470-51-0
Formula :	C₇H₇NOS
M.W :	153.20
SMILES Code :	O=C1NCCC2=C1SC=C2
MDL No. :	MFCD14706770
InChI Key :	ORPWXKFFXAOFCU-UHFFFAOYSA-N
Pubchem ID :	21815346

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Yield	Reaction Conditions	Operation in experiment
71%		Preparation 3; 5,6-Dihydro-4H-thieno[2,3-c]pyridin-7-one; Prepare the title compound by essentially following procedures as found in Aparajithan, K.; Thompson, A. C; Sam, J. J. Heterocyclic. Chem. 1966, 3, 466. Dissolve <strong>[5650-52-2]4,5-dihydro-cyclopenta[b]thiophen-6-one</strong> (Bonini, B. F.; et. al. Eur. J. Org.Chem. 2004, 4442 and references cited therein) (0.658 g, 4.77 mmol) in MeOH (50 mL), and add hydroxylamine hydrochloride (0.365 g, 5.25 mmol) and NaOAc (2.35 g, 28.62 mmol). Stir the reaction at RT overnight. Remove the organic solvent in vacuo, and treat the residue with EtOAc (60 mL). Filter through silica gel, wash with EtOAc, and concentrate. Treat the residue with PPA (30 g), heating to 130 0C in an oil bath and with occasional stirring over 30 min. Allow the reaction to cool to RT and pour into ice water (100 mL). Extract with CH2Cl2 (3 x 150 mL). Wash the combined organic layers with 0.1 M NaOH (100 mL), dry over Na2SO4 and concentrate. Purify the material by chromatography, eluting with 75%EtOAc/hexanes to give 0.521 g (71%) of the title compound. MS/ES m/z 154.1 [M+H]+.
71%	With hydroxylamine hydrochloride; sodium acetate; In methanol; at 20℃;Product distribution / selectivity;	Preparation 19; 5,6-Dihydro-4H-thieno[2,3-c]pyridin-7-one; Prepare the title compound by essentially following procedures as found in Aparajithan, K.; Thompson, A. C; Sam, J. J. Heterocyclic. Chem. 1966, 3, 466. <n="34"/>Dissolve <strong>[5650-52-2]4,5-dihydro-cyclopenta[b]thiophen-6-one</strong> (Bonini, B. F.; et. al. Eur. J. Org. Chem. 2004, 4442 and references cited therein) (0.658 g, 4.77 mmol) in MeOH (50 mL), and add hydroxylamine hydrochloride (0.365 g, 5.25 mmol) and NaOAc (2.35 g, 28.62 mmol). Stir the reaction at RT overnight. Remove the organic solvent in vacuo, and treat the residue with EtOAc (60 mL). Filter through silica gel, wash with EtOAc, and concentrate. Treat the residue with PPA (30 g), heating to 130 0C in an oil bath and with occasional stirring over 30 min. Allow the reaction to cool to RT and pour into ice water (100 mL). Extract with CH2CI2 (3 x 150 mL). Wash the combined organic layers with 0.1 M NaOH (100 mL), dry over Na2SO4 and concentrate. Purify the material by chromatography, eluting with 75%EtOAc/hexanes to give the title compound (0.521 g, 71%). MS/ES m/z 154.1 [M+H]+
55%		A solution of <strong>[5650-52-2]4H-cyclopenta[b]thiophen-6(5H)-one</strong> (1.34 g, 9.7 mmol), hydroxylamine HCl (1.45 g, 20.8 mmol) and NaOAc (7.3 g, 89.0 mmol) in MeOH (150 mL) was stirred overnight at room temperature. The reaction was then concentrated under reduced pressure, taken up in EtOAc (100 mL) and filtered over a plug of silica gel, eluting with EtOAc. The filtrate was concentrated, taken up in polyphosphoric acid (100 g) and heated for 2 h at 130 C. Upon completion, the reaction was quenched by pouring over ice water (100 mL). The aqueous mixture was extracted with DCM (2×100 mL) and the combined extracts were washed with 0.1 M NaOH (100 mL), dried over Na2SO4, then filtered and concentrated. 5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one (837 mg, 55% yield) was isolated as a white solid after purification by flash chromatography over silica gel (20-30% EtOAc/hexane eluent). 1H NMR (300 MHz, MeOH) delta ppm 7.69 (d, J=5.0 Hz, 1H), 7.06 (d, J=5.0 Hz, 1H), 3.57 (t, J=7.1 Hz, 2 H), 2.94 (t, J=7.1 Hz, 2H); MS (EI) m/z=154.2 [M+1]+.

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CAS No.: 14470-51-0

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CAS No.: 14470-51-0

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
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