Sodium hydride → 4-Hydroxy-6-oxo-3-phenyl-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester

HRID 215983Notes

Reaction equation

HRID 215983 reaction equation
C(O[C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][S:8][C:7]=1[NH:17][C:18](=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:5])C.[H-].[Na+]>C1COCC1>[CH2:23]([O:22][C:20]([C:19]1[C:18](=[O:25])[NH:17][C:7]2[S:8][CH:9]=[C:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:6]=2[C:4]=1[OH:5])=[O:21])[CH3:24]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 684322622-(2-Ethoxycarbonyl-acetylamino)-4-phenyl-thiophene-3-carboxylic acid ethyl ester

Product 1

HCID 547275694-Hydroxy-6-oxo-3-phenyl-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Ethoxycarbonyl-acetylamino)-4-phenyl-thiophene-3-carboxylic acid ethyl ester (5.0 g, 13.8 mmol) and sodium hydride (1.1 g, 27.7 mmol) in anhydrous THF (120 ml) were refluxed for 6 hr under nitrogen. On cooling, solvents were removed in vacuo and the residue suspended in water (100 ml). The mixture was acidified by addition of concentrated hydrochloric acid (5 ml) and stirred for 1 hr. The precipitate was filtered and dried, then recrystallised from ethanol to give 4-hydroxy-6-oxo-3-phenyl-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester as a pale yellow solid. Yield=2.59 g (63.3%).

Workup

  1. temperatureOn cooling
  2. customsolvents were removed in vacuo
  3. additionThe mixture was acidified by addition of concentrated hydrochloric acid (5 ml)
  4. filtrationThe precipitate was filtered
  5. customdried
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-dc8aa5c8043e4b7d8c63e7191dea0e2b
Source dataset
uspto-grants-2012_06
Patent number
US08193215B2

Reaction notes

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