Methyl 2,3,3a,4,7,7a-hexahydro-3a-hydroxy-5-methyl-7-(2-nitrophenyl)-1,1-dioxo-thieno[3,2-b]pyridine-6-carboxylate → Methyl 2,3,4,7,-tetrahydro-5-methyl-7-(2-nitrophenyl)-1,1-dioxothieno [3,2-b]pyridine-6-carboxylate

HRID 231345Notes

Reaction equation

HRID 231345 reaction equation
O[C:2]12[CH2:10][CH2:9][S:8](=[O:12])(=[O:11])[CH:7]1[CH:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])[C:5]([C:22]([O:24][CH3:25])=[O:23])=[C:4]([CH3:26])[NH:3]2>C1(C)C=CC=CC=1>[CH3:26][C:4]1[NH:3][C:2]2[CH2:10][CH2:9][S:8](=[O:11])(=[O:12])[C:7]=2[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[C:5]=1[C:22]([O:24][CH3:25])=[O:23]

Participants

3

Reactant 1

HCID 14280858Methyl 2,3,3a,4,7,7a-hexahydro-3a-hydroxy-5-methyl-7-(2-nitrophenyl)-1,1-dioxo-thieno[3,2-b]pyridine-6-carboxylate

Product 1

HCID 14011212Methyl 2,3,4,7,-tetrahydro-5-methyl-7-(2-nitrophenyl)-1,1-dioxothieno [3,2-b]pyridine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 2,3,3a,4,7,7a-hexahydro-3a-hydroxy-5-methyl-7-(2-nitrophenyl)-1,1-dioxothieno[3,2-b]pyridine-6-carboxylate (2.5 g, 0.0065 moles) and toluene (60 mL) was refluxed for 24 hours. The solvent was removed in vacuo and the resulting solid was recrystallized from ethanol. The crystals were washed with diethyl ether 2× and dried at 65° C. under high vacuum for 48 hours. This gave 1.78 g product; mp 215°-217° C.

Workup

  1. temperaturewas refluxed for 24 hours
  2. customThe solvent was removed in vacuo
  3. customthe resulting solid was recrystallized from ethanol
  4. washThe crystals were washed with diethyl ether 2×
  5. customdried at 65° C. under high vacuum for 48 hours

Sources & evidence

ORD record
ord-db781df33b784f95b528df385cf2ba93
Source dataset
uspto-grants-1989_07
Patent number
US04845225

Reaction notes

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